Organization
Institute of Integrated Research Center for Fundamental Research Institute Professor
Title
Institute Professor
External link
SUZUKI KEISUKE
Degree
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Master of Science ( The University of Tokyo, Graduate School of Science )
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Doctor of Science ( The University of Tokyo )
Research Areas
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Life Science / Bioorganic chemistry
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Nanotechnology/Materials / Structural organic chemistry and physical organic chemistry
Education
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The University of Tokyo Graduate School of Science Department of Chemistry
1978.4 - 1983.3
Country： Japan
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The University of Tokyo Faculty of Science Department of Chemistry
1974.4 - 1978.3
Country： Japan
Research History
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Kitasato University Honorary Proffesor
2024.4
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Institute of Science Tokyo Specially Appointed Professor
2020.4
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Tokyo Institute of Technology Honorary Proffesor
2020.4
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The Japan Academy Member
2018.12
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The Open University of Japan Guest Professor
2018.4
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Tokyo Institute of Technology School of Science Department of Chemistry Professor
2016.4 - 2020.3
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Tokyo Institute of Technology Executive Director / Executive Vice-Presiden
2011.10 - 2012.9
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The University of Regensburg (UR) Visiting Professor
2010.4 - 2011.3
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Tokyo Institute of Technology The Graduate School of Science and Technology Professor
1998.4 - 2016.3
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Tokyo Institute of Technology Faculty of Science Professor
1996.4 - 1998.3
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Keio University Faculty of Science and Technology Professor
1994.4 - 1996.3
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Keio University Faculty of Science and Technology Associate Professor
1989.4 - 1993.3
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Swiss Federal Institutes of Technology (SFIT) Visiting Associate Professor
1989.3 - 1990.3
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Keio University Faculty of Science and Technology Lecturer
1987.4 - 1989.3
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Keio University Faculty of Science and Technology Assistant
1983.4 - 1987.3
Professional Memberships
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有機合成協会 会長
2013.1 - 2015.2
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日本化学会
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アメリカ化学会
Papers
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Total Syntheses of β‐ and γ‐Naphthocyclinones
Yoshio Ando, Taiju Hoshino, Nozomi Tanaka, Mark M. Maturi, Yusuke Nakazawa, Takumi Fukazawa, Ken Ohmori, Keisuke Suzuki
Angewandte Chemie International Edition 64 ( 6 ) 2024.11
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Yoshio Ando, Keisuke Suzuki, Mark M. Maturi, Taiju Hoshino, Nozomi Tanaka, Takahiro Sakai, Ken Ohmori
Synlett 2023.7
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Yoshio Ando, Ken Ohmori, Daichi Ogawa, Fumihiro Wakita, Keisuke Suzuki
Synlett 2023.6
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Stereospecific naphthoquinone photoredox reactions: Total syntheses of spirocyclic natural products Reviewed
Yoshio Ando, Keisuke Suzuki
Tetrahedron 139 133448 - 133448 2023.6
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Yoshio Ando, Daichi Ogawa, Ken Ohmori, Keisuke Suzuki
Angewandte Chemie International Edition 62 ( 5 ) 2022.12
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Total Synthesis and Structure Assignment of Saptomycin H Reviewed
Jun Shimura, Yoshio Ando, Ken Ohmori, Keisuke Suzuki
Organic Letters 24 1439 - 1443 2022.2
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Seiya Matsuoka, Kohei Azami, Yusuke Fujiki, Reina Dohi, Tomokazu Yasuike, Ken Ohmori, Keisuke Suzuki
Synlett 32 A - G 2021.9
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Model Study toward Total Synthesis of Dimeric Pyranonaphthoquinones: Synthesis of Hemi-Actinorhodin Reviewed
Yoshio Ando, Takumi Fukazawa, Ken Ohmori, Keisuke Suzuki
Bulletin of the Chemical Society of Japan 94 ( 4 ) 1364 - 1376 2021.4
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Photoredox Reaction of Naphthoquinone C‐Glycoside Revisited: Insight into Stereochemical Aspect Reviewed
Yoshio Ando, Takashi Matsumoto, Keisuke Suzuki
Helvetica Chimica Acta 104 ( 3 ) e2100008 2021.3
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Keisuke Suzuki, Hiroshi Nakakohara, Yoichi Hirano, Ken Ohmori, Hiroshi Takikawa
Synlett 2020.11
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Synthetic Study on Lactonamycins, Part 2: Stereoselective Access to ABCD-Ring System
Hiroshi Takikawa, Kazuki Murata, Shogo Sato, Takuma Kawada, Hiroshi Nakakohara, Ken Ohmori, Keisuke Suzuki
Synlett 31 ( 16 ) 1623 - 1628 2020.10
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Synthetic Study on Lactonamycins, Part 2: Stereoselective Access to ABCD-Ring System
Hiroshi Takikawa, Kazuki Murata, Shogo Sato, Takuma Kawada, Hiroshi Nakakohara, Ken Ohmori, Keisuke Suzuki
SYNLETT 31 ( 16 ) 1623 - 1628 2020.10
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Thiolate-mediated Reductive Cyclizations: Scope, Limitation and Novel Mechanistic Insights Reviewed
Yoshio Ando, Takumi Fukazawa, Ken Ohmori, Keisuke Suzuki
Chemistry Letters 49 ( 9 ) 1103 - 1106 2020.9
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Intramolecular Benzyne-Phenolate [4+2] Cycloadditions. Reviewed International journal
Hiroshi Takikawa, Arata Nishii, Hiromu Takiguchi, Hirotoshi Yagishita, Masato Tanaka, Keiichi Hirano, Masanobu Uchiyama, Ken Ohmori, Keisuke Suzuki
Angewandte Chemie (International ed. in English) 2020.4
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Yoshio Ando, Yoshihiko Maezawa, Jun Shimura, Kei Kitamura, Takashi Matsumoto, Keisuke Suzuki
Chemistry – An Asian Journal 15 ( 6 ) 828 - 832 2020.3
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Synthesis of Enantiopure C-2-Symmetric Anthracenophane and Dimerization En Route to Multiple-Bridged Cyclophanes
Yasuyuki Ueda, Keisuke Suzuki, Ken Ohmori
ORGANIC LETTERS 22 ( 5 ) 2002 - 2006 2020.3
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Hydroxylamine-Mediated Anthrapyranone Formation, Solving 5-exo/6-endo Issue toward Synthesis of Pluramycin-Class Antibiotics Reviewed
Jun Shimura, Yoshio Ando, Keisuke Suzuki
Organic Letters 22 ( 1 ) 175 - 179 2020.1
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α-L-Vancosamine Aryl C-Glycosides, Less Stable Anomers: A Problem in Synthesis of Pluramycin-Class Antibiotics
Keisuke Suzuki, Yoshio Ando, Hiromune Asahina, Kei Kitamura, Takashi Matsumoto
HETEROCYCLES 101 ( 2 ) 645 - 645 2020
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Syntheses of doubly linked proanthocyanidins using free flavan units as nucleophiles: insight into the origin of the high regioselectivity of annulation
Vipul V. Betkekar, Mio Harachi, Keisuke Suzuki, Ken Ohmori
ORGANIC & BIOMOLECULAR CHEMISTRY 17 ( 41 ) 9129 - 9134 2019.11
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Stereochemical Dichotomy in Two Competing Cascade Processes: Total Syntheses of Both Enantiomers of Spiroxin A
Yoshio Ando, Daisuke Tanaka, Ryota Sasaki, Ken Ohmori, Keisuke Suzuki
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 58 ( 36 ) 12507 - 12513 2019.9
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Thiolate-mediated reductive cyclization: asymmetric total synthesis of (+)-engelharquinone
Yoshio Ando, Takumi Fukazawa, Subaru Hori, Ken Ohmori, Keisuke Suzuki
Phosphorus, Sulfur and Silicon and the Related Elements 194 ( 7 ) 723 - 725 2019.7
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Thiolate-mediated reductive cyclization: asymmetric total synthesis of (+)-engelharquinone
Yoshio Ando, Takumi Fukazawa, Subaru Hori, Ken Ohmori, Keisuke Suzuki
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS 194 ( 7 ) 723 - 725 2019.7
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2-Bromo-6-(chlorodiisopropylsilyl)phenyl tosylate as an efficient platform for intramolecular benzyne-diene [4+2] cycloaddition Reviewed
Nishii Arata, Takikawa Hiroshi, Suzuki Keisuke
CHEMICAL SCIENCE 10 ( 13 ) 3840 - 3845 2019.4
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Total Synthesis of Carthamin, a Traditional Natural Red Pigment
Kohei Azami, Taiki Hayashi, Takenori Kusumi, Ken Ohmori, Keisuke Suzuki
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 58 ( 16 ) 5321 - 5326 2019.4
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General Synthetic Approach to Rotenoids via Stereospecific, Group-Selective 1,2-Rearrangement and Dual SNAr Cyclizations of Aryl Fluorides
Seiya Matsuoka, Kayo Nakamura, Ken Ohmori, Keisuke Suzuki
SYNTHESIS-STUTTGART 51 ( 5 ) 1139 - 1156 2019.3
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Total Synthesis of Actinorhodin
Mamiko Ninomiya, Yoshio Ando, Fumitaka Kudo, Ken Ohmori, Keisuke Suzuki
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 58 ( 13 ) 4264 - 4270 2019.3
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Synthetic Strategy toward Dearomatized Polycyclic Polyketide Natural Products Reviewed
Takikawa Hiroshi, Suzuki Keisuke
Journal of Synthetic Organic Chemistry, Japan 77 ( 1 ) 13 - 25 2019
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Aryne-based strategy in the total synthesis of naturally occurring polycyclic compounds Reviewed
Takikawa Hiroshi, Nishii Arata, Sakai Takahiro, Suzuki Keisuke
CHEMICAL SOCIETY REVIEWS 47 ( 21 ) 8030 - 8056 2018.11
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Photoredox Reactions of Quinones Reviewed
Yoshio Ando, Keisuke Suzuki
Chemistry - A European Journal 24 ( 60 ) 15955 - 15964 2018.10
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Intramolecular photoredox reactions of 1,2-naphthoquinone derivatives
Yoshio Ando, Fumihiro Wakita, Ken Ohmori, Keisuke Suzuki
Bioorganic and Medicinal Chemistry Letters 28 ( 16 ) 2663 - 2666 2018.9
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Intramolecular photoredox reactions of 1,2-naphthoquinone derivatives
Yoshio Ando, Fumihiro Wakita, Ken Ohmori, Keisuke Suzuki
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS 28 ( 16 ) 2663 - 2666 2018.9
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Model Reactions for the Enantioselective Synthesis of γ-Rubromycin: Stereospecific Intramolecular Photoredox Cyclization of an ortho-Quinone Ether to a Spiroacetal
Fumihiro Wakita, Yoshio Ando, Ken Ohmori, Keisuke Suzuki
Organic Letters 20 ( 13 ) 3928 - 3932 2018.7
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Total Synthesis of Bis-anthraquinone Antibiotic BE-43472B Reviewed
Yu Yamashita, Yoichi Hirano, Akiomi Takada, Hiroshi Takikawa, Keisuke Suzuki
Synthesis (Germany) 50 ( 13 ) 2490 - 2515 2018.7
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Impact of Green Tea Catechin ECG and Its Synthesized Fluorinated Analogue on Prostate Cancer Cells and Stimulated Immunocompetent Cells
Sven Stadlbauer, Carmen Steinborn, Amy Klemd, Fumihiko Hattori, Ken Ohmori, Keisuke Suzuki, Roman Huber, Philipp Wolf, Carsten Gründemann
Planta Medica 84 ( 11 ) 813 - 819 2018.7
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Model Reactions for the Enantioselective Synthesis of gamma-Rubromycin: Stereospecific Intramolecular Photoredox Cyclization of an ortho-Quinone Ether to a Spiroacetal
Fumihiro Wakita, Yoshio Ando, Ken Ohmori, Keisuke Suzuki
ORGANIC LETTERS 20 ( 13 ) 3928 - 3932 2018.7
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Total Syntheses of Pusilatins A-C, Liverwort-Derived Macrocyclic Bisbibenzyl Dimers
Takahiro Yamada, Hiromu Takiguchi, Ken Ohmori, Keisuke Suzuki
Organic Letters 20 ( 12 ) 3579 - 3582 2018.6
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First Total Synthesis of Oxirapentyn D, a Highly Oxidized Chromene Natural Product
Takahiro Sakai, Keisuke Suzuki, Ken Ohmori
Synlett 29 ( 10 ) 1351 - 1357 2018.6
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Total Synthesis of Selligueain A, a Sweet Flavan Trimer
Yuka Noguchi, Rikako Takeda, Keisuke Suzuki, Ken Ohmori
Organic Letters 20 ( 10 ) 2857 - 2861 2018.5
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Total Synthesis of ArylC-Glycoside Natural Products: Strategies and Tactics Reviewed
Kei Kitamura, Yoshio Ando, Takashi Matsumoto, Keisuke Suzuki
Chemical Reviews 118 ( 4 ) 1495 - 1598 2018.2
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Synthesis of oxygenated orthomethylbenzaldehydes via aryne [2+2] cycloaddition and benzocyclobutenol ring opening
Mark M. Maturi, Ken Ohmori, Keisuke Suzuki
Chimia 72 ( 12 ) 870 - 873 2018
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First Total Syntheses of Tetracenomycins C and X Reviewed
Shogo Sato, Keiichiro Sakata, Yoshimitsu Hashimoto, Hiroshi Takikawa, Keisuke Suzuki
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 56 ( 41 ) 12608 - 12613 2017.10
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Preparation of 2-Substituted 3-Methoxycarbonyl-4-methoxyfurans that Allow Access to Highly Functionalized Naphthalenes via Regioselective Cycloaddition with Alkoxybenzyne Reviewed
Shogo Sato, Takuma Kawada, Hiroshi Takikawa, Keisuke Suzuki
SYNLETT 28 ( 14 ) 1719 - 1723 2017.9
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Oxidative Ring Opening of Benzocyclobutenone Oximes: Novel Access to Stable Nitrile Oxides Reviewed
Hiroshi Takikawa, Shogo Sato, Ryota Seki, Keisuke Suzuki
CHEMISTRY LETTERS 46 ( 7 ) 998 - 1000 2017.7
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Intramolecular Photoredox Reaction of Naphthoquinone Derivatives Reviewed
Yoshio Ando, Takashi Matsumoto, Keisuke Suzuki
SYNLETT 28 ( 9 ) 1040 - 1045 2017.6
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Total Syntheses of Atrovenetin and Atrovenetinone: A Naphthalene-Annulation Approach to a Discoid Tricycle Using Allenic Acid
Kyohei Matsushita, Keisuke Suzuki, Ken Ohmori
Synlett 28 ( 8 ) 944 - 950 2017.5
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Enantioselective Access to Bicyclo[3.2.1]octadienone Skeleton: Total Syntheses of (+)-Engelharquinone and Its Epoxide
Takumi Fukazawa, Yoshio Ando, Ken Ohmori, Tamio Hayashi, Keisuke Suzuki
Organic Letters 19 ( 6 ) 1470 - 1473 2017.3
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Synthetic Study on Carthamin. 2. Stereoselective Approach to C-Glycosyl Quinochalcone via Desymmetrization
Taiki Hayashi, Ken Ohmori, Keisuke Suzuki
Organic Letters 19 ( 4 ) 866 - 869 2017.2
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Synthetic Study on Acremoxanthone A: Construction of Bicyclo [3.2.2]nonane CD Skeleton and Fusion of AB Rings Reviewed
Yoichi Hirano, Kensei Tokudome, Hiroshi Takikawa, Keisuke Suzuki
SYNLETT 28 ( 2 ) 214 - 220 2017.1
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Stereocontrolled Total Syntheses of (−)-Rotenone and (−)-Dalpanol by 1,2-Rearrangement and S<inf>N</inf>Ar Oxycyclizations
Kayo Nakamura, Ken Ohmori, Keisuke Suzuki
Angewandte Chemie - International Edition 56 ( 1 ) 182 - 187 2017
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Stereospecificity in Intramolecular Photoredox Reactions of Naphthoquinones: Enantioselective Total Synthesis of (−)-Spiroxin C
Yoshio Ando, Atsuko Hanaki, Ryota Sasaki, Ken Ohmori, Keisuke Suzuki
Angewandte Chemie - International Edition 56 ( 38 ) 11460 - 11465 2017
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Synthetic Study on Carthamin: Problem and Solution for Oxidative Dearomatization Approach to Quinol C -Glycoside
Taiki Hayashi, Ken Ohmori, Keisuke Suzuki
Synlett 27 ( 16 ) 2345 - 2351 2016.10
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Synthesis of beta-Hydroxynaphthoate Derivatives from Ketodioxinones via Benzyne Acyl-Alkylation and Aldol Condensation Cascade Reviewed
Hiroshi Takikawa, Arata Nishii, Keisuke Suzuki
SYNTHESIS-STUTTGART 48 ( 19 ) 3331 - 3338 2016.10
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Total Synthesis of (+)-Vicenin-2
Thanh C. Ho, Haruki Kamimura, Ken Ohmori, Keisuke Suzuki
Organic Letters 18 ( 18 ) 4488 - 4490 2016.9
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Facile Synthesis of Stereodefined α-Iodovinyl Sulfoxides, Versatile Platform to Trisubstituted Olefins
Sunna Jung, Yasuyuki Ueda, Keisuke Suzuki, Ken Ohmori
Synlett 27 ( 13 ) 2024 - 2028 2016.8
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Pleospdione, A Tricyclic Natural Product with Dense Oxygenation at the A-Ring: Total Synthesis and Incongruity of the Originally Assigned Structure and its C3-Epimer Reviewed
Hiroshi Takikawa, Yui Ishikawa, Yuki Yoshinaga, Yoshimitsu Hashimoto, Takenori Kusumi, Keisuke Suzuki
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN 89 ( 8 ) 941 - 954 2016.8
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Stereocontrolled synthesis of planar chiral carba-paracyclophanes via modular assembly
Sunna Jung, Yoko Kitajima, Yasuyuki Ueda, Keisuke Suzuki, Ken Ohmori
Synlett 27 ( 10 ) 1521 - 1526 2016.6
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Stereocontrolled Synthesis of Planar Chiral Carba-Paracyclophanes via Modular Assembly
Sunna Jung, Yoko Kitajima, Yasuyuki Ueda, Keisuke Suzuki, Ken Ohmori
SYNLETT 27 ( 10 ) 1521 - 1526 2016.6
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First Total Synthesis of Dermocanarin 2 Reviewed
Satoru Yamaguchi, Nobuyuki Takahashi, Daisuke Yuyama, Kayo Sakamoto, Keisuke Suzuki, Takashi Matsumoto
SYNLETT 27 ( 8 ) 1262 - 1268 2016.5
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Asymmetric Total Syntheses of Antibiotic Tetracenomycins Reviewed
Sato Shogo, Sakata Keiichiro, Hashimoto Yoshimitsu, Takikawa Hiroshi, Suzuki Keisuke
Symposium on the Chemistry of Natural Products, symposium papers 58 ( 0 ) Oral24 2016
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Total Synthesis of the Proposed Structure of Ardimerin, and Proposal for its Structural Revision
Ryota Nakayama, Eva Maria Tanzer, Takenori Kusumi, Ken Ohmori, Keisuke Suzuki
Helvetica Chimica Acta 99 ( 12 ) 944 - 960 2016
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Total Syntheses of Perenniporides
Masao Morita, Ken Ohmori, Keisuke Suzuki
Organic Letters 17 ( 22 ) 5634 - 5637 2015.11
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Toward Naphthocyclinones: Doubly Connected Octaketide Dimers with a Bicyclo[3.2.1]octadienone Core by Thiolate-Mediated Cyclization
Yoshio Ando, Subaru Hori, Takumi Fukazawa, Ken Ohmori, Keisuke Suzuki
Angewandte Chemie - International Edition 54 ( 33 ) 9650 - 9653 2015.8
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Synthetic Study on Naphthospironone A: Construction of Benzobicyclo[3.2.1]octene Skeleton with Oxaspirocycle Reviewed
Juri Sakata, Yoshio Ando, Ken Ohmori, Keisuke Suzuki
ORGANIC LETTERS 17 ( 15 ) 3746 - 3749 2015.8
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Procyanidins negatively affect the activity of the phosphatases of regenerating liver Reviewed
Sven Stadlbauer, Pablo Rios, Ken Ohmori, Keisuke Suzuki, Maja Köhn
PLoS ONE 10 ( 7 ) 2015.7
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Dioxanone-fused dienes enable highly endo -selective intramolecular diels-alder reactions
Yoshifumi Aoki, Ken Ohmori, Keisuke Suzuki
Organic Letters 17 ( 11 ) 2756 - 2759 2015.6
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The flavan-isoflavan rearrangement: Bioinspired synthetic access to isoflavonoids via 1,2-shift-alkylation sequence
Kayo Nakamura, Ken Ohmori, Keisuke Suzuki
Chemical Communications 51 ( 32 ) 7012 - 7014 2015.4
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Ambipolar transistor properties of 2,2′-binaphthosemiquinones Reviewed
Toshiki Higashino, Shohei Kumeta, Sumika Tamura, Yoshio Ando, Ken Ohmori, Keisuke Suzuki, Takehiko Mori
Journal of Materials Chemistry C 3 ( 7 ) 1588 - 1594 2015.2
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Stereospecific Photoredox Reaction of Naphthoquinone: Total Synthesis of Spiroxins Reviewed
Ando Yoshio, Hanaki Atsuko, Sasaki Ryota, Matsumoto Takashi, Ohmori Ken, Suzuki Keisuke
Symposium on the Chemistry of Natural Products, symposium papers 57 ( 0 ) Oral25 2015
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Toward the Pluramycins: Route Exploration from Dihydroxyanthrone Tricyclic Platform to an Aglycon, Saptomycinone B Reviewed
Keisuke Suzuki, Takashi Matsumoto, Kei Kitamura, Yoshio Ando, Yoshihiko Maezawa
HETEROCYCLES 90 ( 2 ) 1240 - 1240 2015
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A seco-catechin cyclization approach to 4→6-linked catechin dimers
Gen Watanabe, Ken Ohmori, Keisuke Suzuki
Chemical Communications 50 ( 92 ) 14371 - 14373 2014.10
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Isoxazole Platform for Polyketide Assembly: Cycloaddition of Stable Benzonitrile Oxides to Stable ortho-Quinone Monoacetals and Dehydrogenation Reviewed
Hiroshi Takikawa, Yoshimitsu Hashimoto, Keisuke Suzuki
CHEMISTRY LETTERS 43 ( 10 ) 1607 - 1609 2014.10
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Annulation approach to doubly linked (A-type) oligocatechins: Syntheses of (+)-procyanidin A<inf>2</inf> and (+)-cinnamtannin B<inf>1</inf>
Yuji Ito, Ken Ohmori, Keisuke Suzuki
Angewandte Chemie - International Edition 53 ( 38 ) 10129 - 10133 2014.9
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Synthetic Strategies and Tactics for Catechin and Related Polyphenols
Ken Ohmori, Keisuke Suzuki
Recent Advances in Polyphenol Research 4 371 - 410 2014.8
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Synthesis of the Pluramycins 2: Total Synthesis and Structure Assignment of Saptomycin B Reviewed
Kei Kitamura, Yoshihiko Maezawa, Yoshio Ando, Takenori Kusumi, Takashi Matsumoto, Keisuke Suzuki
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 53 ( 5 ) 1262 - 1265 2014.1
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Synthesis of the Pluramycins 1: Two Designed Anthrones as Enabling Platforms for Flexible Bis-C-Glycosylation Reviewed
Kei Kitamura, Yoshio Ando, Takashi Matsumoto, Keisuke Suzuki
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 53 ( 5 ) 1258 - 1261 2014.1
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Synthetic Strategies and Tactics for Catechin and Related Polyphenols
Ken Ohmori, Keisuke Suzuki
RECENT ADVANCES IN POLYPHENOL RESEARCH, VOL 4 4 371 - 410 2014
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Novel One-Pot Synthesis of Xanthones via Sequential Fluoride Ion-Promoted Fries-Type Rearrangement and Nucleophilic Aromatic Substitution Reviewed
Yuuki Fujimoto, Ryohei Itakura, Hiroki Hoshi, Hikaru Yanai, Yoshio Ando, Keisuke Suzuki, Takashi Matsumoto
SYNLETT 24 ( 19 ) 2575 - 2580 2013.12
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Synthesis and determination of the absolute configuration of cavicularin by a symmetrization/asymmetrization approach
Hiromu Takiguchi, Ken Ohmori, Keisuke Suzuki
Angewandte Chemie - International Edition 52 ( 40 ) 10472 - 10476 2013.9
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First regiocontrolled synthesis of procyanidin B<inf>6</inf>, a catechin dimer with rare connectivity: A halo-capping strategy for formation of 4,6-interflavan bonds
Gen Watanabe, Ken Ohmori, Keisuke Suzuki
Chemical Communications 49 ( 45 ) 5210 - 5212 2013.5
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Preparation of L-vancosamine-related glycosyl donors Reviewed
Kei Kitamura, Masayuki Shigeta, Yoshihiko Maezawa, Yukie Watanabe, Day-Shin Hsu, Yoshio Ando, Takashi Matsumoto, Keisuke Suzuki
JOURNAL OF ANTIBIOTICS 66 ( 3 ) 131 - 139 2013.3
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Total Synthesis of the Antibiotic BE-43472B Reviewed
Yu Yamashita, Yoichi Hirano, Akiomi Takada, Hiroshi Takikawa, Keisuke Suzuki
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 52 ( 26 ) 6658 - 6661 2013
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First Total Synthesis of Dermocanarin 2 Reviewed
Yamaguchi Satoru, Yuyama Daisuke, Takahashi Nobuyuki, Suzuki Keisuke, Matsumoto Takashi
Symposium on the Chemistry of Natural Products, symposium papers 55 ( 0 ) Oral44 2013
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Total Synthesis of Antibiotic BE-43472B Reviewed
Yamashita Yu, Hirano Yoichi, Takada Akiomi, Takikawa Hiroshi, Suzuki Keisuke
Symposium on the Chemistry of Natural Products, symposium papers 55 ( 0 ) Oral26 2013
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Synthesis and structure revision of goupiolone A: A benzotropolone natural product
Nobuaki Fukui, Ken Ohmori, Keisuke Suzuki
Helvetica Chimica Acta 95 ( 11 ) 2194 - 2217 2012.11
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Unified approach to catechin hetero-oligomers: First total synthesis of trimer EZ-EG-CA isolated from Ziziphus jujuba
Takahisa Yano, Ken Ohmori, Haruko Takahashi, Takenori Kusumi, Keisuke Suzuki
Organic and Biomolecular Chemistry 10 ( 38 ) 7685 - 7688 2012.10
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A new synthetic strategy for catechin-class polyphenols: Concise synthesis of (−)-epicatechin and its 3-O-gallate
Sven Stadlbauer, Ken Ohmori, Fumihiko Hattori, Keisuke Suzuki
Chemical Communications 48 ( 67 ) 8425 - 8427 2012.7
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Synthesis of isoxazoles en route to semi-aromatized polyketides: dehydrogenation of benzonitrile oxide-para-quinone acetal cycloadducts Reviewed
Yoshimitsu Hashimoto, Akiomi Takada, Hiroshi Takikawa, Keisuke Suzuki
ORGANIC & BIOMOLECULAR CHEMISTRY 10 ( 30 ) 6003 - 6009 2012
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34 Synthetic Study on Pluramycin-class Antibiotics(Oral Presentation) Reviewed
Kitamura Kei, Maezawa Yoshihiko, Ando Yoshio, Matsumoto Takashi, Suzuki Keisuke
Symposium on the Chemistry of Natural Products, symposium papers 54 ( 0 ) 199 - 204 2012
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Ring Expansion of Cyclopropylbenzocyclobutenes En Route to Benzocycloheptenes
FUKUI Nobuaki, HAMURA Toshiyuki, OHMORI Ken, SUZUKI Keisuke
Chemistry Letters 40 ( 10 ) 1198 - 1200 2011.10
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Total synthesis and structure revision of deacetylravidomycin M
Akimi Ben, Day-Shin Hsu, Takashi Matsumoto, Keisuke Suzuki
TETRAHEDRON 67 ( 35 ) 6460 - 6468 2011.9
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Enantioselective Total Synthesis of (-)-Euxanmodin B: An Axially Chiral Natural Product with an Anthraquinone-Xanthone Composite Structure Reviewed
Nobuyuki Takahashi, Takeshi Kanayama, Kumi Okuyama, Hiroko Kataoka, Haruhiko Fukaya, Keisuke Suzuki, Takashi Matsumoto
CHEMISTRY-AN ASIAN JOURNAL 6 ( 7 ) 1752 - 1756 2011.7
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Integrated synthetic strategy for higher catechin oligomers
Ken Ohmori, Tomohiro Shono, Yuki Hatakoshi, Takahisa Yano, Keisuke Suzuki
Angewandte Chemie - International Edition 50 ( 21 ) 4862 - 4867 2011.5
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Regioselective Remote Functionalization of Biaryl Framework via Tethered ortho-Quinol Intermediate Reviewed
Yasuhito Koyama, Hiroko Kataoka, Keisuke Suzuki, Takashi Matsumoto
CHEMISTRY-AN ASIAN JOURNAL 6 ( 2 ) 355 - 358 2011.2
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Ring expansion approach to azaspiro[4.5]decane skeletons via electrophilic activation of benzocyclobutenols bearing pyridyl group
Taiki Hayashi, Ken Ohmori, Keisuke Suzuki
Chemistry Letters 40 ( 6 ) 612 - 613 2011
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Expeditious modular assembly of multisubstituted cyclohexanes via dioxanonedienes
Yoshifumi Aoki, Yuta Mochizuki, Tomohiro Yoshinari, Ken Ohmori, Keisuke Suzuki
Chemistry Letters 40 ( 10 ) 1192 - 1194 2011
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Total Synthesis and Absolute Stereochemistry of Seragakinone A Reviewed
Akiomi Takada, Yoshimitsu Hashimoto, Hiroshi Takikawa, Katsuyoshi Hikita, Keisuke Suzuki
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 50 ( 10 ) 2297 - 2301 2011
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Regioselective approach to multisubstituted benzenes
Hana Seo, Ken Ohmori, Keisuke Suzuki
Chemistry Letters 40 ( 7 ) 744 - 746 2011
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Concise synthesis of riccardin C, macrocyclic bisbibenzyl natural product
Hiromu Takiguchi, Ken Ohmori, Keisuke Suzuki
Chemistry Letters 40 ( 10 ) 1069 - 1071 2011
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Efficient Bis-C-Aminoglycosylation toward the Synthesis of the Pluramycins Reviewed
Masayuki Shigeta, Tomohiko Hakamata, Yukie Watanabe, Kei Kitamura, Yoshio Ando, Keisuke Suzuki, Takashi Matsumoto
SYNLETT ( 17 ) 2654 - 2658 2010.10
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General synthesis of epi-series catechins and their 3-gallates: Reverse polarity strategy
Ken Ohmori, Takahisa Yano, Keisuke Suzuki
Organic and Biomolecular Chemistry 8 ( 12 ) 2693 - 2696 2010.6
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Synthesis and chiroptical properties of π-conjugated polymer consisting of dihydropentahelicene units with axial chirality
Masahiro Abe, Ken Ohmori, Keisuke Suzuki, Takakazu Yamamoto
Journal of Polymer Science, Part A: Polymer Chemistry 48 ( 8 ) 1844 - 1848 2010.4
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Total synthesis and absolute configuration of macrocidin A, a cyclophane tetramic acid natural product
Tomohiro Yoshinari, Ken Ohmori, Marcus G. Schrems, Andreas Pfaltz, Keisuke Suzuki
Angewandte Chemie - International Edition 49 ( 5 ) 881 - 885 2010.1
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Shinya Shinozaki, Toshiyuki Hamura, Yousuke Ibusuki, Kotaro Fujii, Hidehiro Uekusa, Keisuke Suzuki
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 49 ( 17 ) 3026 - 3029 2010
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Stereochemical relay via axially chiral styrenes: Asymmetric synthesis of the antibiotic tan-1085
Keiji Mori, Ken Ohmori, Keisuke Suzuki
Angewandte Chemie - International Edition 48 ( 31 ) 5633 - 5637 2009.7
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Hydrogen-bond control in axially chiral styrenes: Selective synthesis of enantiomerically pure c<inf>2</inf>-symmetric paracyclophanes
Keiji Mori, Ken Ohmori, Keisuke Suzuki
Angewandte Chemie - International Edition 48 ( 31 ) 5638 - 5641 2009.7
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Enantiodivergent Synthesis of Tetra-ortho-Substituted Biphenyls by Enzymatic Desymmetrization Reviewed
Kumi Okuyama, Koji Shingubara, Shin-ichiro Tsujiyama, Keisuke Suzuki, Takashi Matsumoto
SYNLETT ( 6 ) 941 - 944 2009.4
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First stereoselective total synthesis of FD-594 aglycon
Ritsuki Masuo, Ken Ohmori, Lukas Hintermann, Saki Yoshida, Keisuke Suzuki
Angewandte Chemie - International Edition 48 ( 19 ) 3462 - 3465 2009.4
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First Total Synthesis of (+)-11-Hydroxyerythratidine Reviewed
Toshio Onoda, Yosuke Takikawa, Takashi Fujimoto, Yshizumi Yasui, Keisuke Suzuki, Takashi Matsumoto
SYNLETT ( 7 ) 1041 - 1046 2009.4
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Stereocontolled synthesis of (-)-afzelechin: General route to catechin-class polyphenols by solving an S <inf>N</inf>2 vs. S <inf>N</inf>1 problem
Ken Ohmori, Megumi Takeda, Takashi Higuchi, Tomohiro Shono, Keisuke Suzuki
Chemistry Letters 38 ( 9 ) 934 - 935 2009
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ChemInform Abstract: Total Synthesis and Structure Assignment of the Anthrone C-Glycoside Cassialoin.
Yasuhito Koyama, Ryo Yamaguchi, Keisuke Suzuki
ChemInform 39 ( 23 ) 2008.6
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Total Synthesis and Structure Assignment of the Anthrone C-Glycoside Cassialoin
Yasuhito Koyama, Ryo Yamaguchi, Keisuke Suzuki
Angewandte Chemie 120 ( 6 ) 1100 - 1103 2008.1
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Isoxazole-Assisted Direct Substitution of the Hydroxy Group in alpha-Ketols: Introduction of Angular Substituents in a Polycyclic System Reviewed
Hiroshi Takikawa, Katsuyoshi Hikita, Keisuke Suzuki
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 47 ( 51 ) 9887 - 9890 2008
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Isoxazole-directed pinacol rearrangement: Stereocontrolled approach to angular stereogenic centers Reviewed
Keisuke Suzuki, Hiroshi Takikawa, Yoshifumi Hachisu, Jeffrey W. Bode
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 46 ( 18 ) 3252 - 3254 2007
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P-462 Synthetic Approach to Polyketide-Derived Polycyclic Natural Products with Stereogenic Center at Angular Position
Takikawa Hiroshi, Suzuki Keisuke
International Symposium on the Chemistry of Natural Products 2006 "P - 462" 2006.7
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P-245 Axially Chiral Styrene : Key for the Asymmetric Total Synthesis of TAN-1085
Mori Keiji, Ohmori Ken, Suzuki Keisuke
International Symposium on the Chemistry of Natural Products 2006 "P - 245" 2006.7
-
Reconstruction using bone lengthening of the residual digit after amputation for the treatment of digital malignant tumors Reviewed
C Uchikura, J Hirano, F Kudo, K Mochizuki, K Suzuki, K Satomi
JOURNAL OF ORTHOPAEDIC SCIENCE 11 ( 2 ) 212 - 216 2006.3
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Lipase-catalyzed asymmetrization of diacetate of meso-2-(2-propynyl)cyclohexane-1,2,3-triol toward the total synthesis of aquayamycin Reviewed
T Matsumoto, T Konegawa, H Yamaguchi, T Nakamura, T Sugai, K Suzuki
SYNLETT ( 10 ) 1650 - 1652 2001.10
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Regioselective alkylzirconation of internal alkynes Reviewed
S Yamanoi, K Seki, T Matsumoto, K Suzuki
JOURNAL OF ORGANOMETALLIC CHEMISTRY 624 ( 1-2 ) 143 - 150 2001.4
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Novel insight into photochromism and thermochromism of hydrogen bonded schiff bases Reviewed
T., Suzuki, T., Arai
Chemistry Letters 124-125 2001.1
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Regioselectivity of MAO-catalyzed allylmetallation of conjugated enynes with allylzirconiums
S Yamanoi, T Matsumoto, K Suzuki
TETRAHEDRON LETTERS 39 ( 52 ) 9727 - 9730 1998.12
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Total synthesis of the furaquinocins Reviewed
T Saito, T Suzuki, M Morimoto, C Akiyama, T Ochiai, K Takeuchi, T Matsumoto, K Suzuki
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 120 ( 45 ) 11633 - 11644 1998.11
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Base-promoted ring expansion of 2-alkoxy-2-vinylbenzocyclobutenol into substituted naphthalene derivatives
T Matsumoto, T Hamura, M Miyamoto, K Suzuki
TETRAHEDRON LETTERS 39 ( 27 ) 4853 - 4856 1998.7
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Unusual regioselectivity in the reductive coupling of alkynes and allenes by hydrozirconation and zinca-Claisen rearrangement Reviewed
K Suzuki, T Imai, S Yamanoi, M Chino, T Matsumoto
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH 36 ( 22 ) 2469 - 2471 1997.12
-
Isochroman-3-ones via Site-selective Ring Opening of Benzocyclobutenones promoted by Lithium Tetramethylpiperidide and Reaction with Aromatic Aldehyde
T. Matsumoto, T. Hamura, Y. Kuriyama, K. Suzuki
Tetrahedron Letters 38 ( 52 ) 8985 - 8988 1997
-
1,2-アニオノトロピー反応の新しい転位基:コバルト錯体の形成によるアルキニル基の1,2移動の促進
鈴木啓介
アメリカ化学会誌 118 8949 1997
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C-Glycosyl Juglone in Angucycline Synthesis : Total Synthesis of Galtamycinone, Common Aglycone of C-Glycosyl Naphthacenequinone-Type Angucyclines.
Takashi Matsumoto, Hiroki, Yamaguchi, Keisuke Suzuki
Tetrahedron 53 ( 48 ) 16533 1997
-
MAO-Catalyzed. Allylzirconation of 1-Alkynes
Shigeo Yamanoi, Takahiro Imai, Takashi Matsumoto, Keisuke Suzuki
Tetrahedron Letters 38 ( 17 ) 3031 - 3034 1997
-
Implication and Improvement of Stereoselective Methylenation of a Chiral Aldehyde Related to Total Synthesis of the Furaquinocins
Takeshi Saito, Takao Suzuki Kazuhiro, Takeuchi Takashi, Matsumoto, Keisuke Suzuki
Tetrahedron Letters 38 ( 21 ) 3755 - 3758 1997
-
Total synthesis of galtamycinone, the common aglycon of the C-glycosyl naphthacenequinone antibiotics Reviewed
T Matsumoto, H Yamaguchi, K Suzuki
SYNLETT ( 5 ) 433 - & 1996.5
-
Hydrozirconation of allenyl sulfide for generating gamma-thio-substituted allylzirconium species and its reaction with carbonyl compounds
M Chino, GH Liang, T Matsumoto, K Suzuki
CHEMISTRY LETTERS 1996 ( 3 ) 231 - 232 1996
-
C-GLYCOSYLATION-CYCLOADDITION APPROACH TO C-GLYCOSYL JUGLONES - VERSATILE INTERMEDIATES TOWARD ARYL C-GLYCOSIDE ANTIBIOTICS Reviewed
T MATSUMOTO, T SOHMA, H YAMAGUCHI, K SUZUKI
CHEMISTRY LETTERS ( 8 ) 677 - 678 1995.8
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Benzyne-Furan Cycloaddition Approach to the Angucyclines: First Total Synthesis of Antibiotic C104
T. Matsumoto, T. Sohma, H. Yamaguchi, K. Suzuki
Synlett 1995 ( 3 ) 263 - 266 1995
-
Total Synthesis of Antibiotic C104: Benzyne–Furan Cycloaddition Approach to the Angucyclines
T. Matsumoto, T. Sohma, H. Yamaguchi, K. Suzuki
Tetrahedron 51 ( 27 ) 7347 - 7360 1995
-
Convenient Procedure for Selective Generation of Allylzirconocene Chlorides via Hydrozirconation of Allenes
M. Chino, T. Matsumoto, K. Suzuki
Synlett 1994 ( 5 ) 359 - 363 1994
-
DIBUTYLTIN DIPERCHLORATE FOR ACTIVATION OF GLYCOSYL FLUORIDE
H MAETA, T MATSUMOTO, K SUZUKI
CARBOHYDRATE RESEARCH 249 ( 1 ) 49 - 56 1993.10
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DEUTERIUM-ISOTOPE EFFECTS ON AROMATIC C-13 CHEMICAL-SHIFTS .5. NONADDITIVITY OF METHYL SUBSTITUENT EFFECTS ON ONE-BOND ISOTOPE SHIFTS FOR METHYLPYRIDINE N-OXIDES Reviewed
Y NAKASHIMA, M FUKUNAGA, K SUZUKI, K TAKAHASHI
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN 66 ( 8 ) 2143 - 2148 1993.8
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New Methods in Glycoside Synthesis by Using Early Transition Metal-Derived Reagent. Reviewed
SUZUKI Keisuke, MATSUMOTO Takashi
Journal of Synthetic Organic Chemistry, Japan 51 ( 8 ) 718 - 732 1993
-
TRANS-1,3-BIS(DIPHENYLPHOSPHINOYL)CYCLOHEXANE Reviewed
M MOROOKA, T HASHIMOTO, H MAETA, T MATSUMOTO, K SUZUKI, S OHBA
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS 48 1710 - 1712 1992.9
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EFFICIENT METHOD FOR INTRODUCING VINEOMYCIN-FRIDAMYCIN-TYPE SIDE-CHAIN - TOTAL SYNTHESIS OF FRIDAMYCIN-E Reviewed
T MATSUMOTO, H JONA, M KATSUKI, K SUZUKI
TETRAHEDRON LETTERS 32 ( 38 ) 5103 - 5106 1991.9
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CONVERGENT TOTAL SYNTHESIS OF VINEOMYCINONE-B2 METHYL-ESTER AND ITS C(12)-EPIMER
T MATSUMOTO, M KATSUKI, H JONA, K SUZUKI
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 113 ( 18 ) 6982 - 6992 1991.8
-
CRYSTAL-STRUCTURE OF HEAD-TO-HEAD BIS(MU-ALPHA-PYRIDONATO-N,O)BIS[(ETHYLENEDIAMINE)PALLADIUM] NITRATE, [PD2(EN)2(C5H4NO)2](NO3)2, AND C-13 AND H-1-C-13 COSY NMR-STUDY OF HEAD-TO-HEAD TO HEAD-TO-TAIL ISOMERIZATION IN SOLUTION Reviewed
K MATSUMOTO, H MORIYAMA, K SUZUKI
INORGANIC CHEMISTRY 29 ( 11 ) 2096 - 2100 1990.5
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New reagents. VI. Reagents for glycosylation. Cp2MCl2-AgX(M=Zr,Hr): A reagent for glycosidation. Reviewed
SUZUKI Keisuke, MATSUMOTO Takashi
Journal of Synthetic Organic Chemistry, Japan 48 ( 11 ) 1026 - 1027 1990
-
RAPID O-GLYCOSIDATION OF PHENOLS WITH GLYCOSYL FLUORIDE BY USING THE COMBINATIONAL ACTIVATOR, CP2HFCL2-AGCLO4
T MATSUMOTO, M KATSUKI, K SUZUKI
CHEMISTRY LETTERS 1989 ( 3 ) 437 - 440 1989.3
-
SYNTHESIS AND CRYSTAL-STRUCTURE OF HEAD-TO-HEAD BIS(MU-2-PYRIDONATO-N,O)BIS[(ETHYLENEDIAMINE)PALLADIUM] NITRATE, [PD2(EN)2(C5H4NO)2](NO3)2 Reviewed
K SUZUKI, K MATSUMOTO
CHEMISTRY LETTERS ( 2 ) 317 - 320 1989.2
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AN IMPROVED PROCEDURE FOR METALLOCENE-PROMOTED GLYCOSIDATION - ENHANCED REACTIVITY BY EMPLOYING 1-2-RATIO OF CP2HFCL2-AGCLO4 Reviewed
K SUZUKI, H MAETA, T MATSUMOTO
TETRAHEDRON LETTERS 30 ( 36 ) 4853 - 4856 1989
-
CP2ZRCL2-AGCLO4 - EFFICIENT PROMOTER FOR THE FRIEDEL-CRAFTS APPROACH TO C-ARYL GLYCOSIDES Reviewed
T MATSUMOTO, M KATSUKI, K SUZUKI
TETRAHEDRON LETTERS 30 ( 7 ) 833 - 836 1989
-
SYNTHETIC STUDY TOWARD VINEOMYCINS - SYNTHESIS OF C-ARYL GLYCOSIDE SECTOR VIA CP2HFCL2-AGCLO4-PROMOTED TACTICS Reviewed
T MATSUMOTO, M KATSUKI, H JONA, K SUZUKI
TETRAHEDRON LETTERS 30 ( 45 ) 6185 - 6188 1989
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CP2ZRCL2-AGBF4 IN BENZENE - A NEW REAGENT SYSTEM FOR RAPID AND HIGHLY SELECTIVE ALPHA-MANNOSIDE SYNTHESIS FROM TETRA-O-BENZYL-D-MANNOSYL FLUORIDE Reviewed
K SUZUKI, H MAETA, T SUZUKI, T MATSUMOTO
TETRAHEDRON LETTERS 30 ( 49 ) 6879 - 6882 1989
-
New Glycosidation Reaction 1. Combinational Use of Cp2ZrCl2-AgClO4 for Activation of Glycosyl Fluorides and Application to Highly b-Selective Glycosidation of D-Mycinose
T. Matsumoto, H. Maeta, K. Suzuki, G. Tsuchihashi
Tetrahedron Letters 29 ( 29 ) 3567 - 3570 1988
-
New Glycosidation Reaction 2. Preparation of 1-Fluoro-D-Desosamine Derivative and Its Efficient Glycosidation by the Use of CpHfCl2-AgClO4 as the Activator
K. Suzuki, H. Maeta, T. Matsumoto, G. Tsuchihashi
Tetrahedron Letters 29 ( 29 ) 3571 - 3574 1988
-
Highly Selective Acyclic Stereocontrol Based on 1, 2-Rearrangement
Keisuke Suzuki
Journal of Synthetic Organic Chemistry, Japan 46 ( 4 ) 367 - 377 1988
-
First Total Synthesis of Mycinamicin IV and VII. Successful Application of New Glycosidation Reaction
T. Matsumoto, H. Maeta, K. Suzuki, G. Tsuchihashi
Tetrahedron Letters 29 ( 29 ) 3575 - 3578 1988
-
New Approach to C-Aryl Glycosides Starting from Phenol and Glycosyl Fluoride. Lewis Acid-Catalyzed Rearrangement of O-Glycoside to C-Glycoside
T. Matsumoto, M. Katsuki, K. Suzuki
Tetrahedron Letters 29 ( 52 ) 6935 - 6938 1988
-
STEREOCONTROLLED 1ST TOTAL SYNTHESIS OF MYCINOLIDE-IV Reviewed
K SUZUKI, T MATSUMOTO, K TOMOOKA, K MATSUMOTO, G TSUCHIHASHI
CHEMISTRY LETTERS ( 1 ) 113 - 116 1987
-
STEREOSELECTIVE SYNTHESIS OF C(1)-C(9) AND C(11)-C(17) FRAGMENTS OF PROTOMYCINOLIDE-IV BASED ON ASYMMETRIC PINACOL-TYPE REARRANGEMENT Reviewed
K SUZUKI, K TOMOOKA, T MATSUMOTO, E KATAYAMA, G TSUCHIHASHI
TETRAHEDRON LETTERS 26 ( 31 ) 3711 - 3714 1985
-
HIGHLY STEREOSELECTIVE APPROACH TO CHIRAL BUILDING BLOCK POSSESSING 3 CONTIGUOUS ASYMMETRIC CENTERS - PREPARATION OF 4 POSSIBLE DIASTEREOMERS OF "BETA,BETA'-DIMETHYL-BIS-HOMOALLYLIC ALCOHOL DERIVATIVE Reviewed
K SUZUKI, E KATAYAMA, K TOMOOKA, T MATSUMOTO, G TSUCHIHASHI
TETRAHEDRON LETTERS 26 ( 31 ) 3707 - 3710 1985
-
Reductive Pinacol-Type Rearrangement of a-Mesyloxy Ketones Promoted by Organoaluminum Compounds
K. Suzuki, E. Katayama, T. Matsumoto, G. Tsuchihashi
Tetrahedron Letters 25 ( 34 ) 3715 - 3718 1984
Books
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理工系学生のための基礎化学
鈴木, 啓介, 後藤, 敬, 豊田, 真司, 大森, 建
化学同人 2023.4 （ ISBN:9784759811261 ）
-
分子構造と反応・有機金属化学
野依, 良治, 中筋, 一弘, 玉尾, 皓平, 奈良坂, 紘一, 柴崎, 正勝, 橋本, 俊一, 鈴木, 啓介, 山本, 陽介, 村田, 道雄
東京化学同人 2019.3 （ ISBN:9784807908202 ）
-
初歩からの化学
安池, 智一, 鈴木, 啓介
放送大学教育振興会 2018.3 （ ISBN:9784595319013 ）
-
天然有機化合物の合成戦略
鈴木, 啓介
岩波書店 2017.1 （ ISBN:9784007305665 ）
-
有機合成化学・生物有機化学
野依, 良治, 中筋, 一弘, 玉尾, 皓平, 奈良坂, 紘一, 柴崎, 正勝, 橋本, 俊一, 鈴木, 啓介, 山本, 陽介, 村田, 道雄
東京化学同人 2015.10 （ ISBN:9784807908219 ）
-
(Dichlorobis(cyclopentadienyl)hafnium, CAS No: 12116-66-4 Update)
WILEY 2009
-
天然有機化合物の合成戦略
鈴木, 啓介
岩波書店 2007.11 （ ISBN:9784000110402 ）
-
有機分子触媒の新展開
シーエムシー出版 2007
-
太田, 博道, 鈴木, 啓介
裳華房 2004 （ ISBN:9784785332112 ）
-
天然物合成の今昔 ー 分子パズルの変遷、
先端化学シリーズ、海洋天然物/錯体/コンビナトリアル/全合成、丸善 2003
-
ペリ環状反応 : 第三の有機反応機構
Fleming, Ian, 鈴木, 啓介, 千田, 憲孝
化学同人 2002.6 （ ISBN:4759808752 ）
-
Cationic Zirconocene Species in Organic Synthesis, in Titanium and Zirconium in Organic Synthesis, I. Marek Ed., Chapter 8
Wiley-VCH 2002
-
Arene Analogs of the Heck Reaction, in Handbook of Organopalladium Chemistry for Organic Synthesis, E. Negishi, Ed.
John Wiley & Sons 2002
-
Cationic Zirconocene Species in Organic Synthesis, in Titanium and Zirconium in Organic Synthesis, I. Marek Ed., Chapter 8
Wiley-VCH 2002
-
Arene Analogs of the Heck Reaction, in Handbook of Organopalladium Chemistry for Organic Synthesis, E. Negishi, Ed.
John Wiley & Sons 2002
-
生物活性天然物の合成 : 複雑な構造をいかにして構築するか
桑嶋, 功, 伊藤, 嘉彦, 奈良坂, 紘一, 鈴木, 啓介
東京化学同人 2000.3 （ ISBN:4807913360 ）
-
Kirby, Anthony J. (Anthony John), 鈴木, 啓介
化学同人 1999.1 （ ISBN:9784759808193 ）
-
大学院講義有機化学 I. 分子構造と反応・有機金属化学
東京化学同人 1999
-
大学院講義有機化学 II. 有機合成化学・生物有機化学
東京化学同人 1998
MISC
-
Intramolecular Photoredox Reaction of Naphthoquinone Derivatives (vol 28, pg 1040, 2017)
Yoshio Ando, Takashi Matsumoto, Keisuke Suzuki
SYNLETT 28 ( 9 ) E4 - E4 2017.6
-
Synthetic strategies and tactics for oligomeric proanthocyanidins
Ken Ohmori, Keisuke Suzuki
Current Organic Chemistry 16 ( 5 ) 566 - 577 2012.3
-
Anti-selective vinylogous aldol reaction by silylated alkyldioxinone dienolate
Tomohiro Yoshinari, Ken Ohmori, Keisuke Suzuki
Chemistry Letters 39 ( 10 ) 1042 - 1044 2010
-
Total Synthesis and Absolute Stereochemistry of Seragakinone A
Takada Akiomi, Takikawa Hiroshi, Hikita Katsuyoshi, Hashimoto Yoshimitsu, Suzuki Keisuke
Symposium on the Chemistry of Natural Products, symposium papers 52 ( 0 ) 115 - 120 2010
-
Solvent-Controlled Leaving-Group Selectivity in Aromatic Nucleophilic Substitution
Lukas Hintermann, Ritsuki Masuo, Keisuke Suzuki
ORGANIC LETTERS 10 ( 21 ) 4859 - 4862 2008.11
-
2,5-dihydroxyterephthalates, 2,5-dichloro-1,4-benzoquinone-3,6-dicarboxylates, and polymorphic 2,5-dichloro-3,6-dihydroxyterephthalates
Lukas Hintermann, Keisuke Suzuki
SYNTHESIS-STUTTGART ( 14 ) 2303 - 2306 2008.7
-
Linearly fused dicyclobutabenzenes via dual, regioselective cycloadditions of 1,4-benzdiyne equivalent and ketene silyl Acetals
Tetsu Arisawa, Toshiyuki Hamura, Hidehiro Uekusa, Takashi Matsumoto, Keisuke Suzuki
SYNLETT ( 8 ) 1179 - 1184 2008.5
-
Synthesis and stereochemical assignment of angucycline antibiotic, PD-116740
Keiji Mori, Yuuya Tanaka, Ken Ohmori, Keisuke Suzuki
CHEMISTRY LETTERS 37 ( 4 ) 470 - 471 2008.4
-
Formation of alpha-hydroxy-beta-diketones through hydroxylation of isoxazolium salts: Stereoselective approach to angular cis-diols in polycyclic systems
Hiroshi Takikawa, Akionii Takada, Katsuyoshi Hikita, Keisuke Suzuki
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 47 ( 39 ) 7446 - 7449 2008
-
Total Synthesis and Structure Assignment of the Anthrone C-Glycoside Cassialoin
Y. Koyama, R. Yamaguchi, KEISUKE SUZUKI
Angew. Chem. Int. Ed. 47 ( 6 ) 1084 - 1087 2008
-
Formation of alpha-hydroxy-beta-diketones through hydroxylation of isoxazolium salts: Stereoselective approach to angular cis-diols in polycyclic systems
Hiroshi Takikawa, Akionii Takada, Katsuyoshi Hikita, Keisuke Suzuki
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 47 ( 39 ) 7446 - 7449 2008
-
Ring selectivity: Successive ring expansion of two benzocyclobutenes for divergent access to angular and linear benzanthraquinones
Takeaki Suzuki, Toshiyuki Hamura, Keisuke Suzuki
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 47 ( 12 ) 2248 - 2252 2008
-
Total Synthesis and Structure Assignment of the Anthrone C-Glycoside Cassialoin
Y. Koyama, R. Yamaguchi, KEISUKE SUZUKI
Angew. Chem. Int. Ed. 47 ( 6 ) 1084 - 1087 2008
-
Total synthesis and structure assignment of the anthrone C-glycoside cassialoin
Yasuhito Koyama, Ryo Yamaguchi, Keisuke Suzuki
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 47 ( 6 ) 1084 - 1087 2008
-
Synthesis of highly functionalized isoxazoles via base-promoted cyclocondensation of stable nitrile oxides with active methylene compounds
Hiroshi Takikawa, Katsuyoshi Hikita, Keisuke Suzuki
SYNLETT ( 14 ) 2252 - 2256 2007.9
-
27 The Asymmetric Total Synthesis of TAN-1085
Mori Keiji, Ohmori Ken, Suzuki Keisuke
Symposium on the Chemistry of Natural Products, symposium papers ( 49 ) 157 - 162 2007.8
-
Modified chiral triazolium salts for enantioselective benzoin cyclization of enolizable keto-aldehydes: Synthesis of (+)-sappanone B
Hiroshi Takikawa, Keisuke Suzuki
ORGANIC LETTERS 9 ( 14 ) 2713 - 2716 2007.7
-
Mukaiyama aldol reaction of ester acceptors: Organoaluminums catalyze nucleophilic addition of ketene silyl acetals
Shin Iwata, Toshiyuki Hamura, Takashi Matsumoto, Keisuke Suzuki
CHEMISTRY LETTERS 36 ( 4 ) 538 - 539 2007.4
-
Stereoselective access to functionalized dihydrophenanthrenes via reductive cyclization of biaryl ene-aldehydes
Minoru Tamiya, Corinna Jaeger, Ken Ohmori, Keisuke Suzuki
SYNLETT ( 5 ) 780 - 784 2007.3
-
Stereoselective access to functionalized dihydrophenanthrenes via reductive cyclization of biaryl ene-aldehydes
Minoru Tamiya, Corinna Jaeger, Ken Ohmori, Keisuke Suzuki
SYNLETT Vol. ( 5 ) 780 - 784 2007.3
-
Studies on organic synthesis inspired by carbohydrates
Keisuke Suzuki
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN 65 ( 3 ) 175 - 182 2007.3
-
Two isolable conformers of dihydropentahelicenediol derivatives: Stereochemical property and its utility for asymmetric reactions
Ken Ohmori, Sanae Furuya, Shigeo Yamanoi, Keisuke Suzuki
CHEMISTRY LETTERS 36 ( 2 ) 328 - 329 2007.2
-
Two isolable conformers of dihydropentahelicenediol derivatives: Stereochemical property and its utility for asymmetric reactions
Ken Ohmori, Sanae Furuya, Shigeo Yamanoi, Keisuke Suzuki
CHEMISTRY LETTERS 36 ( 2 ) 328 - 329 2007.2
-
General synthesis route to benanomicin-pradimicin antibiotics
Minoru Tamiya, Ken Ohmori, Mitsuru Kitamura, Hirohisa Kato, Tadamasa Arai, Mami Oorui, Keisuke Suzuki
CHEMISTRY-A EUROPEAN JOURNAL 13 ( 35 ) 9791 - 9823 2007
-
Preparation of benzocyclobutenone derivatives based on an efficient generation of benzynes (Bicyclo[4.2.0]octa-1,3,5-trien-7-one, 5-(phenylmethoxy)-)
Shin-ichiro Tsujiyama, Keisuke Suzuki, David B. Guthrie, Heather M. Gibney, Dennis P. Curran
Organic Syntheses 84 ( No. ) 272 - 284 2007
-
General synthesis route to benanomicin-pradimicin antibiotics
Minoru Tamiya, Ken Ohmori, Mitsuru Kitamura, Hirohisa Kato, Tadamasa Arai, Mami Oorui, Keisuke Suzuki
CHEMISTRY-A EUROPEAN JOURNAL 13 ( 35 ) 9791 - 9823 2007
-
Studies on organic synthesis inspired by carbohydrates
Keisuke Suzuki
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry 65 ( 3 ) 175 - 182 2007
-
Preparation of benzocyclobutenone derivatives based on an efficient generation of benzynes (Bicyclo[4.2.0]octa-1,3,5-trien-7-one, 5-(phenylmethoxy)-)
Shin-ichiro Tsujiyama, Keisuke Suzuki, David B. Guthrie, Heather M. Gibney, Dennis P. Curran
Organic Syntheses 84 ( No. ) 272 - 284 2007
-
Modified Chiral Triazolium Salts for Enantioselective Benzoin Cyclization of Enolizable Keto-aldehydes: Synthesis of (+)-Sappanone B
H. Takikawa, KEISUKE SUZUKI
Org. Lett. 9 ( 14 ) 2713 - 2716 2007
-
General synthesis route to benanomicin-pradimicin antibiotics
Minoru Tamiya, Ken Ohmori, Mitsuru Kitamura, Hirohisa Kato, Tadamasa Arai, Mami Oorui, Keisuke Suzuki
CHEMISTRY-A EUROPEAN JOURNAL 13 ( 35 ) 9791 - 9823 2007
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Convergence in [2+2+2] synthesis of β-phenylnaphthalene motif in polyaromatic natural products
Isao Takemura, Koreaki Imura, Takashi Matsumoto, Keisuke Suzuki
Tetrahedron Letters 47 ( 37 ) 6673 - 6676 2006.9
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Facile one-pot synthesis of resorcinol bis-C-glycosides possessing two identical sugar moieties
Takahito Yamauchi, Yukie Watanabe, Keisuke Suzuki, Takashi Matsumoto
SYNTHESIS-STUTTGART ( 17 ) 2818 - 2824 2006.9
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Impressive changeover of reaction course in ring expansion of styrylbenzocyclobutenol under alkoxide-forming conditions
Isao Takemura, Takashi Matsumoto, Keisuke Suzuki
TETRAHEDRON LETTERS 47 ( 37 ) 6677 - 6679 2006.9
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Convergence in [2+2+2] synthesis of beta-phenylnaphthalene motif in polyaromatic natural products
Isao Takemura, Koreaki Imura, Takashi Matsumoto, Keisuke Suzuki
TETRAHEDRON LETTERS 47 ( 37 ) 6673 - 6676 2006.9
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General and convenient approach to flavan-3-ols: Stereoselective synthesis of (-)-gallocatechin
Takashi Higuchi, Ken Ohmori, Keisuke Suzuki
CHEMISTRY LETTERS 35 ( 9 ) 1006 - 1007 2006.9
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Facile one-pot synthesis of resorcinol bis-C-glycosides possessing two identical sugar moieties
Takahito Yamauchi, Yukie Watanabe, Keisuke Suzuki, Takashi Matsumoto
SYNTHESIS-STUTTGART ( 17 ) 2818 - 2824 2006.9
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General and convenient approach to flavan-3-ols: Stereoselective synthesis of (-)-gallocatechin
Takashi Higuchi, Ken Ohmori, Keisuke Suzuki
CHEMISTRY LETTERS 35 ( 9 ) 1006 - 1007 2006.9
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Dodecamethoxy- and hexaoxotricyclobutabenzene: Synthesis and characterization
Toshiyuki Hamura, Yousuke Ibusuki, Hidehiro Uekusa, Takashi Matsumoto, Jay S. Siegel, Kim K. Baldridge, Keisuke Suzuki
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 128 ( 31 ) 10032 - 10033 2006.8
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Peri-selectivity in thermolysis of acyloxybenzocyclobutenes possessing alpha,beta-unsaturated carbonyl group: Synthesis of 2-benzoxocin derivatives
Toshiyuki Hamura, Nobuyuki Kawano, Takashi Matsumoto, Keisuke Suzuki
CHEMISTRY LETTERS 35 ( 7 ) 730 - 731 2006.7
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Poly-oxygenated tricyclobutabenzenes via repeated [2+2] cycloaddition of benzyne and ketene silyl acetal
T Hamura, Y Ibusuki, H Uekusa, T Matsumoto, K Suzuki
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 128 ( 11 ) 3534 - 3535 2006.3
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Synthesis of L-vancosamine derivatives from methyl α-D- mannopyranoside
Day-Shin Hsu, Takashi Matsumoto, Keisuke Suzuki
Synlett ( 3 ) 469 - 471 2006.2
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Bis-C-glycosylation of resorcinol derivatives by an O -> C-glycoside rearrangement
T Yamauchi, Y Watanabe, K Suzuki, T Matsumoto
SYNLETT ( 3 ) 399 - 402 2006.2
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Bis-C-glycosylation of resorcinol derivatives by an O -> C-glycoside rearrangement
T Yamauchi, Y Watanabe, K Suzuki, T Matsumoto
SYNLETT ( 3 ) 399 - 402 2006.2
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Synthesis of L-vancosamine derivatives from methyl alpha-D-mannopyranoside
DS Hsu, T Matsumoto, K Suzuki
SYNLETT ( 3 ) 469 - 471 2006.2
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Sc(OTf)3-catalyzed C-Glycosylation of β-Diketones. A Facile Access to Useful Precursors of Heteroaromatic C-Glycosides
T. Yamauchi, M, Shigeta T, Matsumoto, K. Suzuki
Heterocycles 66 153 - 160 2006
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Sc(OTf)3-catalyzed C-Glycosylation of β-Diketones. A Facile Access to Useful Precursors of Heteroaromatic C-Glycosides
T. Yamauchi, M, Shigeta T, Matsumoto, K. Suzuki
Heterocycles 66 153 - 160 2006
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Synthesis of functionalized tricyclobutabenzenes via repeated [2+2] cycloaddition of benzyne Reviewed
HAMURA TOSHIYUKI, IBUSUKI YOUSUKE, SHINOZAKI SHINYA, MATSUMOTO TAKASHI, SUZUKI KEISUKE
Abstracts of Symposium on Physical Organic Chemistry 18 ( 0 ) 59 - 59 2006
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Peri-selectivity in Thermolysis of Acyloxybenzocyclobutenes Possessing α,β-Unsaturated Carbonyl Group: Synthesis of 2-Benzoxin Derivatives
T. Hamura, N. Kawano, T, Matsumoto, K. Suzuki
Chem. Lett. 35 ( 7 ) 730 - 731 2006
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Catalytic enantioselective crossed aldehyde-ketone benzoin cyclization
Hiroshi Takikawa, Yoshifumi Hachisu, Jeffrey W. Bode, Keisuke Suzuki
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 45 ( 21 ) 3492 - 3494 2006
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Concise Synthesis of (+/－)-γ-Indomycinone
D.-S. Hsu, T, Matsumoto, K. Suzuki
Chem. Lett. 35 ( 9 ) 1016 - 1017 2006
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Impressive Changeover of the Reaction Course in Ring Enlargement of Vinylbenzocyclobutenol
I. Takemura, K. Imura T, Matsumoto, K. Suzuki
Tetrahedron Lett. 47 ( 37 ) 6677 - 6679 2006
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鈴木啓介
化学と生物 44 ( 2 ) 135 - 141 2006
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Concise Synthesis of (+/－)-γ-Indomycinone
D.-S. Hsu, T, Matsumoto, K. Suzuki
Chem. Lett. 35 ( 9 ) 1016 - 1017 2006
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Poly-oxygenated Tricyclobutabenzenes via Repeated [2+2] Cycloaddition of Benzyne and Ketene Silyl Acetal
T. Hamura, Y. Ibusuki, H, Uekusa T, Matsumoto, K. Suzuki
J. Am. Chem. Soc. 128 ( 11 ) 3534 - 3535 2006
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Catalytic enantioselective crossed aldehyde-ketone benzoin cyclization
Hiroshi Takikawa, Yoshifumi Hachisu, Jeffrey W. Bode, Keisuke Suzuki
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 45 ( 21 ) 3492 - 3494 2006
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Two-directional annelation: Dual benzyne cycloadditions starting from bis(sulfonyloxy)diiodobenzene
Toshiyuki Hamura, Tetsu Arisawa, Takashi Matsumoto, Keisuke Suzuki
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 45 ( 41 ) 6842 - 6844 2006
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Tandem ring expansion of alkenyl benzocyclobutenol derivatives into substituted naphthols
Toshiyuki Hamura, Takeaki Suzuki, Takashi Matsumoto, Keisuke Suzuki
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 45 ( 38 ) 6294 - 6296 2006
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Synthesis of (+/-)-lotthanongine, a novel natural product with a flavan-indole hybrid structure
K Hatakeyama, K Ohmori, K Suzuki
SYNLETT ( 8 ) 1311 - 1315 2005.5
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Synthesis of (+/-)-lotthanongine, a novel natural product with a flavan-indole hybrid structure
K Hatakeyama, K Ohmori, K Suzuki
SYNLETT ( 8 ) 1311 - 1315 2005.5
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Efficient synthetic route to ravidosamine derivatives
Day-Shin Hsu, Takashi Matsumoto, Keisuke Suzuki
Synlett ( 5 ) 801 - 804 2005.3
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Efficient synthetic route to ravidosamine derivatives
DS Hsu, T Matsumoto, K Suzuki
SYNLETT ( 5 ) 801 - 804 2005.3
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Regio- and stereocontrolled total synthesis of benanomicin B
K Ohmori, M Tamiya, M Kitamura, H Kato, M Oorui, K Suzuki
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 44 ( 25 ) 3871 - 3874 2005
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Thiazolium ylide-catalyzed intramolecular aldehyde-ketone benzoin-forming reactions: Substrate scope
Y Hachisu, JW Bode, K Suzuki
ADVANCED SYNTHESIS & CATALYSIS 346 ( 9-10 ) 1097 - 1100 2004.8
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Oligomeric catechins: An enabling synthetic strategy by orthogonal activation and C(8) protection
K Ohmori, N Ushimaru, K Suzuki
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA 101 ( 33 ) 12002 - 12007 2004.8
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Concise three-component synthesis of defucogilvocarcin M
Takemura, I, K Imura, T Matsumoto, K Suzuki
ORGANIC LETTERS 6 ( 15 ) 2503 - 2505 2004.7
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Concise three-component synthesis of defucogilvocarcin M
Takemura, I, K Imura, T Matsumoto, K Suzuki
ORGANIC LETTERS 6 ( 15 ) 2503 - 2505 2004.7
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A novel approach to erythrinan alkaloids by utilizing substituted biphenyl as building block
Y Yasui, Y Koga, K Suzuki, T Matsumoto
SYNLETT ( 4 ) 615 - 618 2004.3
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Transmission of axial chirality to spiro center chirality, enabling enantiospecific access to erythrinan alkaloids
Y Yasui, K Suzuki, T Matsumoto
SYNLETT ( 4 ) 619 - 622 2004.3
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Transmission of axial chirality to spiro center chirality, enabling enantiospecific access to erythrinan alkaloids
Y Yasui, K Suzuki, T Matsumoto
SYNLETT ( 4 ) 619 - 622 2004.3
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Sc(OTf)(3) as efficient catalyst for aryl C-glycoside synthesis
A Ben, T Yamauchi, T Matsumoto, K Suzuki
SYNLETT ( 2 ) 225 - 230 2004.2
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Cationic zirconocene- or hafnocene-based Lewis acids in organic synthesis: glycoside-flavonoid analogy
K Ohmori, K Hatakeyama, H Ohrui, K Suzuki
TETRAHEDRON 60 ( 6 ) 1365 - 1373 2004.2
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Cationic zirconocene- or hafnocene-based Lewis acids in organic synthesis: glycoside-flavonoid analogy
K Ohmori, K Hatakeyama, H Ohrui, K Suzuki
TETRAHEDRON 60 ( 6 ) 1365 - 1373 2004.2
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Concise total synthesis and structure assignment of TAN-1085
K Ohmori, K Mori, Y Ishikawa, H Tsuruta, S Kuwahara, N Harada, K Suzuki
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 43 ( 24 ) 3167 - 3171 2004
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Strain-induced regioselectivities in reactions of benzyne possessing a fused four-membered ring
T Hamura, Y Ibusuki, K Sato, T Matsumoto, Y Osamura, K Suzuki
ORGANIC LETTERS 5 ( 20 ) 3551 - 3554 2003.10
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38 Total Synthesis of TAN-1085
OHMORI Ken, ISHIKAWA Yuji, MORI Keiji, TSURUTA Hideyuki, SUZUKI Keisuke
Symposium on the Chemistry of Natural Products, symposium papers ( 45 ) 221 - 226 2003.9
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Catalytic intramolecular crossed aldehyde-ketone benzoin reactions: A novel synthesis of functionalized preanthraquinones
Y Hachisu, JW Bode, K Suzuki
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 125 ( 28 ) 8432 - 8433 2003.7
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Structural incongruities of coleophomone natural products: Insights by total synthesis of a semi-synthetic derivative
Jeffrey W. Bode, Keisuke Suzuki
Tetrahedron Letters 44 ( 17 ) 3559 - 3563 2003.4
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Amine-promoted cyclocondensation of highly substituted aromatic nitrile oxides with diketones
JW Bode, Y Hachisu, T Matsuura, K Suzuki
TETRAHEDRON LETTERS 44 ( 17 ) 3555 - 3558 2003.4
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Structural incongruities of coleophomone natural products: insights by total synthesis of a semi-synthetic derivative
JW Bode, K Suzuki
TETRAHEDRON LETTERS 44 ( 17 ) 3559 - 3563 2003.4
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Isoxazole -> benzisoxazole rearrangement promoted cascade reactions affording stereodefined polycycles
JW Bode, H Uesuka, K Suzuki
ORGANIC LETTERS 5 ( 4 ) 395 - 398 2003.2
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Facile construction and divergent transformation of polycyclic isoxazoles: Direct access to polyketide architectures
JW Bode, Y Hachisu, T Matsuura, K Suzuki
ORGANIC LETTERS 5 ( 4 ) 391 - 394 2003.2
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Facile one-pot procedure for Et3Al-promoted asymmetric pinacol-type rearrangement
T Shinohara, K Suzuki
SYNTHESIS-STUTTGART ( 1 ) 141 - 146 2003.1
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Synthesis of functionalized biaryl compounds via ring expansion of alkenylcyclobutenones
T Hamura, M Morita, T Matsumoto, K Suzuki
TETRAHEDRON LETTERS 44 ( 1 ) 167 - 170 2003.1
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Facile one-pot procedure for Et3Al-promoted asymmetric pinacol-type rearrangement
T Shinohara, K Suzuki
SYNTHESIS-STUTTGART ( 1 ) 141 - 146 2003.1
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Structural Incongruities of Coleophomone Natural Products: Insights by Total Synthesis of a Semi-Synthetic Derivative
J. W. Bode, K. Suzuki
Tetrahedron Lett. 44 ( 17 ) 3559 - 3563 2003
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Stereoselective substitution of flavan skeletons: synthesis of dryopteric acid
K Ohmori, N Ushimaru, K Suzuki
TETRAHEDRON LETTERS 43 ( 43 ) 7753 - 7756 2002.10
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Single-step synthesis of cyclooctadienone derivatives by reaction of alkenylcyclobutenones with alkenyllithiums: Enhanced reactivity of 8 pi cyclization by acetylating the intermediary lithium tetraenolate
T Hamura, N Kawano, T Matsumoto, K Suzuki
CHEMISTRY LETTERS ( 10 ) 1042 - 1043 2002.10
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Single-step synthesis of cyclooctadienone derivatives by reaction of alkenylcyclobutenones with alkenyllithiums: Enhanced reactivity of 8 pi cyclization by acetylating the intermediary lithium tetraenolate
T Hamura, N Kawano, T Matsumoto, K Suzuki
CHEMISTRY LETTERS ( 10 ) 1042 - 1043 2002.10
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Semi-pinacol strategy for constructing B-ring of pradimicin-benanomicin antibiotics
K Ohmori, M Kitamura, Y Ishikawa, H Kato, M Oorui, K Suzuki
TETRAHEDRON LETTERS 43 ( 39 ) 7023 - 7026 2002.9
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Pinacol rearrangement for constructing asymmetric centers adjacent to heterocycles
T Shinohara, K Suzuki
TETRAHEDRON LETTERS 43 ( 39 ) 6937 - 6940 2002.9
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Pinacol rearrangement for constructing asymmetric centers adjacent to heterocycles
T Shinohara, K Suzuki
TETRAHEDRON LETTERS 43 ( 39 ) 6937 - 6940 2002.9
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Single step synthesis of cyclooctadienone derivatives by reaction of cyclobutenones with dienyllithium
T Hamura, S Tsuji, T Matsumoto, K Suzuki
CHEMISTRY LETTERS ( 7 ) 750 - 751 2002.7
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Synthesis of functionalized cyclobutene derivatives via selective S(N)2' reaction of dichlorocyclobutenes
T Hamura, M Kakinuma, S Tsuji, T Matsumoto, K Suzuki
CHEMISTRY LETTERS ( 7 ) 748 - 749 2002.7
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Single step synthesis of cyclooctadienone derivatives by reaction of cyclobutenones with dienyllithium
T Hamura, S Tsuji, T Matsumoto, K Suzuki
CHEMISTRY LETTERS ( 7 ) 750 - 751 2002.7
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Stereochemical anomaly in the thermal conversion of 7,8-dioxy-7-alkenylbenzocyclobutenes to dihydronaphthalenes
T Hamura, M Miyamoto, K Imura, T Matsumoto, K Suzuki
ORGANIC LETTERS 4 ( 10 ) 1675 - 1678 2002.5
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Synthesis of benzocyclooctene derivatives via thermal ring expansion of dienylbenzocyclobutenes
T Hamura, S Tsuji, T Matsumoto, K Suzuki
CHEMISTRY LETTERS ( 3 ) 280 - 281 2002.3
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Synthesis of benzocyclooctene derivatives via thermal ring expansion of dienylbenzocyclobutenes
T Hamura, S Tsuji, T Matsumoto, K Suzuki
CHEMISTRY LETTERS ( 3 ) 280 - 281 2002.3
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Stereogenic tert-alcohols via group-selective hydroalumination: further scope
K Ohmori, Y Hachisu, T Suzuki, K Suzuki
TETRAHEDRON LETTERS 43 ( 6 ) 1031 - 1034 2002.2
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Stereogenic tert-alcohols via group-selective hydroalumination: further scope
K Ohmori, Y Hachisu, T Suzuki, K Suzuki
TETRAHEDRON LETTERS 43 ( 6 ) 1031 - 1034 2002.2
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Facile and highly enantioselective synthesis of axially chiral biaryls by enzymatic desymmetrization
T Matsumoto, T Konegawa, T Nakamura, K Suzuki
SYNLETT 2002 ( 1 ) 122 - 124 2002.1
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Synthesis of hindered 1-arylnaphthalene derivatives via ring expansion of benzocyclobutenones
T Hamura, M Miyamoto, T Matsumoto, K Suzuki
ORGANIC LETTERS 4 ( 2 ) 229 - 232 2002.1
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Facile access to versatile polyaromatic building blocks: Selectively protected benzocyclobutenedione derivatives via regioselective [2+2] cycloaddition of alpha-alkoxybenzyne and ketene silyl acetal
T Hamura, T Hosoya, H Yamaguchi, Y Kuriyama, M Tanabe, M Miyamoto, Y Yasui, T Matsumoto, K Suzuki
HELVETICA CHIMICA ACTA 85 ( 11 ) 3589 - 3604 2002
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Facile access to versatile polyaromatic building blocks: Selectively protected benzocyclobutenedione derivatives via regioselective [2+2] cycloaddition of alpha-alkoxybenzyne and ketene silyl acetal
T Hamura, T Hosoya, H Yamaguchi, Y Kuriyama, M Tanabe, M Miyamoto, Y Yasui, T Matsumoto, K Suzuki
HELVETICA CHIMICA ACTA 85 ( 11 ) 3589 - 3604 2002
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Pseudo-C-3-symmetric tertiary alcohol building block via group-selective hydroalumination: A synthesis of (-)-malyngolide
T Suzuki, K Ohmori, K Suzuki
ORGANIC LETTERS 3 ( 11 ) 1741 - 1744 2001.5
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Group-selective hydroalumination: A novel route to stereogenic tert-alcohol centers
K Ohmori, T Suzuki, K Taya, D Tanabe, T Ohta, K Suzuki
ORGANIC LETTERS 3 ( 7 ) 1057 - 1060 2001.4
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Group-selective hydroalumination: A novel route to stereogenic tert-alcohol centers
K Ohmori, T Suzuki, K Taya, D Tanabe, T Ohta, K Suzuki
ORGANIC LETTERS 3 ( 7 ) 1057 - 1060 2001.4
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Convenient procedure for one-pot conversion of azides to N-monomethylamines
H Kato, K Ohmori, K Suzuki
SYNLETT 2001 1003 - 1005 2001
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Alkylzirconation
S. Yamanoi, K, Seki T, Matsumoto, K. Suzuki
J. Organomet. Chem. 624 143 - 150 2001
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Synthetic study of aquayamycin. Part 1: Synthesis of 3-(phenylsulfonyl)phthalides possessing a beta-C-olivoside
T Matsumoto, H Yamaguchi, T Hamura, M Tanabe, Y Kuriyama, K Suzuki
TETRAHEDRON LETTERS 41 ( 43 ) 8383 - 8387 2000.10
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Synthetic study of aquayamycin. Part 3. First total synthesis
T Matsumoto, H Yamaguchi, M Tanabe, Y Yasui, K Suzuki
TETRAHEDRON LETTERS 41 ( 43 ) 8393 - 8396 2000.10
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Synthetic study of aquayamycin. Part 2. Synthesis of the AB ring fragment
H Yamaguchi, T Konegawa, M Tanabe, T Nakamura, T Matsumoto, K Suzuki
TETRAHEDRON LETTERS 41 ( 43 ) 8389 - 8392 2000.10
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Synthetic study of ravidomycin, a hybrid natural product
K Suzuki
PURE AND APPLIED CHEMISTRY 72 ( 9 ) 1783 - 1786 2000.9
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Glycosylation study on pradimicin-benanomicin antibiotics
H Kato, K Ohmori, K Suzuki
TETRAHEDRON LETTERS 41 ( 35 ) 6827 - 6832 2000.8
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First synthesis of astilbin, biologically active glycosyl flavonoid isolated from Chinese folk medicine
K Ohmori, H Ohrui, K Suzuki
TETRAHEDRON LETTERS 41 ( 29 ) 5537 - 5541 2000.7
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Silicon-directed regioselective [2+2] cycloaddition of alpha-alkoxybenzyne and ketene silyl acetals
T Hosoya, T Hamura, Y Kuriyama, M Miyamoto, T Matsumoto, K Suzuki
SYNLETT ( 4 ) 520 - 522 2000.4
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Total synthesis of ravidomycin: revision of absolute and relative stereochemistry
S Futagami, Y Ohashi, K Imura, T Hosoya, K Ohmori, T Matsumoto, K Suzuki
TETRAHEDRON LETTERS 41 ( 7 ) 1063 - 1067 2000.2
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Thermodynamic and kinetic properties of trans-3,4,5,6-tetramethyl-9,10-dihydroxy-9,10-dihydrophenanthrene: Pseudo-rotational barriers around biphenyl axis
H Kato, K Ohmori, K Suzuki
CHIRALITY 12 ( 5-6 ) 548 - 550 2000
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Synthetic study of ravidomycin, a hybrid natural product
Keisuke Suzuki
Pure and Applied Chemistry 72 ( 9 ) 1783 - 1786 2000
-
Thermodynamic and kinetic properties of trans-3,4,5,6-tetramethyl-9,10-dihydroxy-9,10-dihydrophenanthrene: Pseudo-rotational barriers around biphenyl axis
H Kato, K Ohmori, K Suzuki
CHIRALITY 12 ( 5-6 ) 548 - 550 2000
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Alkylzirconation of alkynes catalyzed by triphenylcarbenium tetrakis(pentafluorophenyl)borate
S Yamanoi, H Ohrui, K Seki, T Matsumoto, K Suzuki
TETRAHEDRON LETTERS 40 ( 48 ) 8407 - 8410 1999.11
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Divergent behavior of cobalt-complexed enyne having a leaving group
Mitsuru Kitamura, Ken Ohmori, Keisuke Suzuki
Tetrahedron Letters 40 ( 24 ) 4563 - 4566 1999.6
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Reaction of 1-iodoalkynes with allylzirconiums: Generation of alkylidene carbenoid via allylzirconation
S Yamanoi, T Matsumoto, K Suzuki
TETRAHEDRON LETTERS 40 ( 14 ) 2793 - 2796 1999.4
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From axial chirality to central chiralities: Pinacol cyclization of 2,2 '-biaryldicarbaldehyde to trans-9,10-dihydrophenanthrene-9,10-diol
K Ohmori, M Kitamura, K Suzuki
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 38 ( 9 ) 1226 - 1229 1999
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Total synthesis of pradimicinone, the common aglycon of the pradimicin-benanomicin antibiotics
M Kitamura, K Ohmori, T Kawase, K Suzuki
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 38 ( 9 ) 1229 - 1232 1999
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Total synthesis of pradimicinone, the common aglycon of the pradimicin-benanomicin antibiotics
M Kitamura, K Ohmori, T Kawase, K Suzuki
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 38 ( 9 ) 1229 - 1232 1999
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28 Synthetic Studies on Pradimicin-Benanomicin Antibiotics
KITAMURA Mitsuru, OHMORI Ken, KAWASE Toshihisa, KATO Hirohisa, SUZUKI Keisuke
Symposium on the Chemistry of Natural Products, symposium papers ( 40 ) 163 - 168 1998.8
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MAO-catalyzed allylzirconation of 1-alkynes (vol 38, pg 3031, 1997)
S Yamanoi, T Imai, T Matsumoto, K Suzuki
TETRAHEDRON LETTERS 38 ( 32 ) 5573 - 5573 1997.8
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Reductive Coupling of Alkynes and Allenes via Hydrozirconation and Zinca-Claisen Rearrangemeut : Unusual Regioselectivity and Application to 1,5-Asymmetric Induction
KEISUKE SUZUKI
Angew. Chem., Int. Ed. Engl. 36 2569 1997
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ヒドロジルコニウム化と亜鉛クライゼン転位を経由するアルキンとアレンの還元的カップリング:特異な位置選択性と1,5-不斉誘起への応用
鈴木啓介
36 2569 1997
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Novel migrating group in 1,2-anionotropic reactions: Cobalt complexation facilitates 1,2-shift of alkynyl groups
Tetsuya Nagasawa, Kimiko Taya, Mitsuru Kitamura, Keisuke Suzuki
Journal of the American Chemical Society 118 ( 37 ) 8949 - 8950 1996.9
-
Total Syntheses of BE-12406 A and Its C(8)-Vinyl Analog.
T. Hosoya, E. Takashiro, Y. Yamamoto, T, Matsumoto, K. Suzuki
Heterocycles 42 ( 1 ) 397 - 414 1996
-
On the Stereochemistry of Aryl C-Glycosides: Unusual Behavior of Bis-TBDPS Protected Aryl C-Olivosides.
T. Hosoya, Y. Ohashi T, Matsumoto, K. Suzuki
Tetrahedron Lett. 37 ( 5 ) 663 - 666 1996
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COBALT-COMPLEXATION MAKES 2-(1-ALKYNYL)PROPENES GOOD ENE DONORS IN CARBONYL-ENE REACTION
T NAGASAWA, M KITAMURA, K SUZUKI
SYNLETT ( 11 ) 1183 - & 1995.11
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SHORT-STEP TOTAL SYNTHESIS OF A CYCLOPROPANE-CONTAINING EICOSANOID
T NAGASAWA, Y ONOGUCHI, T MATSUMOTO, K SUZUKI
SYNLETT ( 10 ) 1023 - & 1995.10
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Total Synthesis of (+/-)- Furaquinocin D
KEISUKE SUZUKI
J.Am.Chem.Soc. 117 10757 1995
-
Total Synthesis of the Gilvocarcins.
K. Suzuki, T, Matsumoto, T. Hosoya
J. Synth. Org. Chem., Jpn. 53 ( 11 ) 1045 - 1054 1995
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16 Total Synthesis of the Furaquinocins
Saito Takeshi, Morimoto Munetsugu, Akiyama Chikako, Matsumoto Takashi, Suzuki Keisuke
Symposium on the Chemistry of Natural Products, symposium papers 37 ( 0 ) 91 - 96 1995
-
Convenient Synthesis of Phthalides via Regioselective Baeyer-Villiger Oxidation of Benzocyclobutenones.
T. Hosoya, Y. Kuriyama, K. Suzuki
Synlett ( 6 ) 635 - 638 1995
-
Stereospecificity in [2 + 2] Cycloaddition of Benzyne and Ketene Silyl Acetal.
T. Hosoya, T. Hasegawa, Y. Kuriyama, K. Suzuki
Tetrahedron Lett. 36 ( 19 ) 3377 - 3380 1995
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Stereocontrolled Convergent Total Synthesis of (±)-Furaquinocin D
Takeshi Saito, Munetsugu Morimoto, Chikako Akiyama, Takashi Matsumoto, Keisuke Suzuki
Journal of the American Chemical Society 117 ( 43 ) 10757 - 10758 1995
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[2 + 2] Cycloaddition of Benzyne and Ketene Silyl Acetal as an Efficient Route to Benzocyclobutenones.
T. Hosoya, T, Hasegawa, Y, Kuriyama T, Matsumoto, K. Suzuki
Synlett ( 2 ) 177 - 179 1995
-
Novel Lewis acid catalysis in organic synthesis
Keisuke Suzuki
Pure and Applied Chemistry 66 ( 7 ) 1557 - 1564 1994.1
-
First Total Synthesis of BE-12406 A.
T. Hosoya, E. Takashiro T, Matsumoto, K. Suzuki
Tetrahedron Lett. 35 ( 26 ) 4591 - 4594 1994
-
Total Synthesis of the Gilvocarcins
KEISUKE SUZUKI
J.Am.Chem.Soc. 116 ( 3 ) 1004 - 1015 1994
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ON THE REGIOCHEMISTRY OF CYCLOADDITION OF UNSYMMETRICAL ARYNE WITH NITRONE REMARKABLE EFFECT OF TRIALKYSILYL SUBSTITUENT
T MATSUMOTO, T SOHMA, S HATAZAKI, K SUZUKI
SYNLETT ( 11 ) 843 - 846 1993.11
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SYNTHESIS OF 1,3-BIS(DIPHENYLPHOSPHINOYL)ALKANES VIA DOUBLE ADDITION OF DIPHENYLPHOSPHINE TO ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS - SEQUENTIAL 1,4-ADDITION AND 1,2-ADDITION PROMOTED BY NBCL5-BF3.OET2
T HASHIMOTO, H MAETA, T MATSUMOTO, M MOROOKA, S OHBA, K SUZUKI
SYNLETT ( 4 ) 340 - 342 1992.4
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TOTAL SYNTHESIS AND ABSOLUTE STEREOCHEMICAL ASSIGNMENT OF GILVOCARCIN-M
T MATSUMOTO, T HOSOYA, K SUZUKI
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 114 ( 9 ) 3568 - 3570 1992.4
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LEWIS ACID PROMOTED REACTION OF SECONDARY PHOSPHINES WITH CARBONYL-COMPOUNDS - REMARKABLE EFFECT OF NIOBIUM(V) CHLORIDE IN PROMOTING AN INTRAMOLECULAR OXIDATION REDUCTION PROCESS
K SUZUKI, T HASHIMOTO, H MAETA, T MATSUMOTO
SYNLETT ( 2 ) 125 - 128 1992.2
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AN ALTERNATIVE SYNTHETIC ROUTE TO THE C(11)-C(17)-FRAGMENT OF MYCINOLIDE-IV
K TOMOOKA, K MATSUMOTO, K SUZUKI, G TSUCHIHASHI
SYNLETT ( 2 ) 129 - 130 1992.2
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Recent Progress in O-Glycoside Synthesis-Methodological Aspects
Keisuke Suzuki, Tetsuya Nagasawa
Journal of Synthetic Organic Chemistry, Japan 50 ( 5 ) 378 - 390 1992
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20 Total Synthesis of Gilvocarcin Antibiotics
Matsumoto Takashi, Hosoya Takamitsu, Takashiro E., Hayakawa K., Suzuki Keisuke
Symposium on the Chemistry of Natural Products, symposium papers 34 ( 0 ) 150 - 157 1992
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NEW EFFICIENT PROTOCOL FOR ARYNE GENERATION - SELECTIVE SYNTHESIS OF DIFFERENTIALLY PROTECTED 1,4,5-NAPHTHALENETRIOLS
T MATSUMOTO, T HOSOYA, M KATSUKI, K SUZUKI
TETRAHEDRON LETTERS 32 ( 46 ) 6735 - 6736 1991.11
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O-]C-GLYCOSIDE REARRANGEMENT OF RESORCINOL DERIVATIVES - VERSATILE INTERMEDIATES IN THE SYNTHESIS OF ARYL C-GLYCOSIDES
T MATSUMOTO, T HOSOYA, K SUZUKI
SYNLETT ( 10 ) 709 - 711 1991.10
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Efficient method for introducing vineomycin-fridamycin-type side chain. Total synthesis of fridamycin E
Takashi Matsumoto, Hideki Jona, Miyoko Katsuki, Keisuke Suzuki
Tetrahedron Letters 32 ( 38 ) 5103 - 5106 1991.9
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ORTHO-METALATION OF ANTHRACENE DERIVATIVE - PROBLEM AND SOLUTION
T MATSUMOTO, H KAKIGI, K SUZUKI
TETRAHEDRON LETTERS 32 ( 34 ) 4337 - 4340 1991.8
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O→C-Glycoside Rearrangement of Resorcinol Derivatives. Versatile Intermediates in the Sysnthesis of Aryl C-Glycosides
KEISUKE SUZUKI
Synlett 1991 1991
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4-O-BENZYL-2,3-O-ISOPROPYLIDENE-L-THREOSE - A USEFUL BUILDING BLOCK FOR STEREOSELECTIVE SYNTHESIS OF MONOSACCHARIDES
T MUKAIYAMA, K SUZUKI, T YAMADA, F TABUSA
TETRAHEDRON 46 ( 1 ) 265 - 276 1990
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Improvement in O→C-Glycoside Rearrangement Approach to C-Aryl Glycosides: Use of 1-O-Acetyl Sugar as Stable but Efficient Glycosyl Donor.
T. Matsumoto, T. Hosoya, K. Suzuki
Tetrahedron Lett. 31 ( 32 ) 4629 - 4632 1990
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69 Total Synthesis of Vineomycin-Fridamycin Antibiotics
Matsumoto Takashi, Katsuki Miyoko, Jona Hideki, Hosoya Takamitsu, Kakigi Hirotoshi, Suzuki Keisuke
Symposium on the Chemistry of Natural Products, symposium papers 32 ( 0 ) 517 - 524 1990
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27 Synthesis of C-Aryl Glycosides Using Metallocene Complex as the Promoter Reviewed
Matsumoto Takashi, Katsuki Miyoko, Jona Hideki, Suzuki Keisuke
Symposium on the Chemistry of Natural Products, symposium papers 31 ( 0 ) 197 - 204 1989
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Stereocontrolled asymmetric total synthesis of protomycinolide IV
Keisuke Suzuki, Katsuhiko Tomooka, Eiji Katayama, Takashi Matsumoto, Gen Ichi Tsuchihashi
Journal of the American Chemical Society 108 5221 - 5229 1986.12
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73 MACROLIDE SYNTHESIS BASED ON STEREOSPECIFIC 1,2-REARRANGEMENT
Suzuki Keisuke, Tomooka Katsuhiko, Matsumoto Takashi, Katayama Eiji, Tsuchihashi Gen-ichi
Symposium on the Chemistry of Natural Products, symposium papers 28 ( 0 ) 566 - 573 1986
Presentations
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Isoxazole-directed Pinacol Rearrangement: Stereo-controlled Approach to Angular Quaternary Stereogenic Centers in Fused Polycyclic Natural Products
Angew. Chem. Int. Ed 2007
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Isoxazole-directed Pinacol Rearrangement: Stereo-controlled Approach to Angular Quaternary Stereogenic Centers in Fused Polycyclic Natural Products
Angew. Chem. Int. Ed 2007
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天然有機化合物の合成戦略
岩波書店 2007
Awards
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藤原賞
2020
鈴木啓介
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The Priize of The Japan Academy
2015.6 The Japan Academy
Keisuke Suzuki
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Medal with Purple Ribbon
2010.11 Japanese Emperor/Government
Keisuke Suzuki
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Humboldt Research Award
2008.6 Alexander von Humboldt Foundation
Keisuke Suzuki
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日本化学会賞
2008
鈴木啓介
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Prizes for Science and Technology
2006 Ministry of Education, Culture, Sport, Science and Technology, Japan
Keisuke Suzuki
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有機合成化学協会賞
2003
鈴木啓介
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名古屋シルバーメダル
1999
鈴木啓介
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手島記念研究論文賞
1997
鈴木啓介
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日本IBM科学賞
1994.11
鈴木啓介
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研究企画賞
1994 有機合成化学協会
鈴木啓介
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高砂香料工業研究企画賞
1993
鈴木啓介
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日本化学会進歩賞
1986
鈴木啓介
Research Projects
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Studies on Chemical Synthesis of Polyketide-Derived, Biologically Active Complex Natural Products
Grant number：16H06351 2016.5 - 2021.3
Japan Society for the Promotion of Science Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (S)
Suzuki Keisuke
Grant amount：\184340000 （ Direct Cost: \141800000 、 Indirect Cost：\42540000 ）
The project on “Studies on Chemical Synthesis of Polyketide-Derived, Biologically Active Complex Natural Products” has been performed at the total synthesis of various complex natural products derived from type-II polyketide biosynthesis. Particular focus was laid on the natural process of evolving the structure diversity and complexity, trying to gain inspiration in developing new synthetic strategies and tactics in organic synthesis. More specifically, we focused three biosynthetic processes by which molecular complexity is enhanced, 1) oxidative structure modification, 2) oligomerization, and 3) hybridization, and aimed at the realization of these complexity/diversity-generating processes in chemical synthesis. Throughout the five-year research, we have succeeded in developing several synthetic routes to some useful/interesting classes of bioactive molecules.
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Controlled Synthesis and Development of Higher-order Functional Biomass Polyphenols
Grant number：16H04107 2016.4 - 2019.3
Japan Society for the Promotion of Science Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (B)
Ohmori Ken, Suzuki Keisuke, Misaka Takumi
Grant amount：\17030000 （ Direct Cost: \13100000 、 Indirect Cost：\3930000 ）
Although natural polyphenols have long played a part in human life as ingredients of wine, tea, or herbal medicines, it was only recently that their biological functions have been unveiled at the molecular level. The realization that specific interactions of polyphenols with biomolecules, such as proteins, exert powerful biological activities has stimulated the search for new pharmaceutical entities derived from polyphenolic entities. These investigations, however, are often hampered by the difficulty in isolating the requisite compounds in pure and structurally defined form, largely because their procurement has relied on natural sources, e.g., plant extracts. This study successfully offers one of synthetic solutions to provide such compounds, in particular, doubly-linked oligomeric flavans. The present study is based on an orthogonal synthetic strategy coupled with an annulation method, enabling efficient accesses to various types of flavan oligomers.
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特異な多環構造を有する天然有機化合物の合成研究
Grant number：16H02258 2016.4 - 2017.3
日本学術振興会 科学研究費助成事業 基盤研究(A)
鈴木 啓介
Grant amount：\46020000 （ Direct Cost: \35400000 、 Indirect Cost：\10620000 ）
本研究事業はH28年度４月より同５月まで、正味２ヶ月の研究期間で実施されたものである。
まず、特異な環構造を有する天然有機化合物の合成に関し、ポリケチド由来の多環芳香族骨格の構築法の開発を目的として、検討を進めた。その結果、アレニルカルボン酸やマロン酸誘導体を基本単位とした環形成反応に関し幾つかの有用な知見を得ることができた。さらに、ニトリルオキシドとキノイド系化合物の反応においては、複雑な酸化様式を有する脱芳香型多環ポリケチド系化合物の合成に繋がりうる初期的知見を得た。 -
Development of Efficient Synthetic Transformation based on Intramolecular Redox Reaction
Grant number：24350021 2012.4 - 2016.3
Japan Society for the Promotion of Science Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (B)
Ohmori Ken, SUZUKI Keisuke, ANDO Yoshio
Grant amount：\18330000 （ Direct Cost: \14100000 、 Indirect Cost：\4230000 ）
This research project focused on development of new synthetic strategy and tactics focusing on intra-molecular redox transformations. Three research topics are addressed. At first, retro-[4+2] cycloaddition reaction for enolsilyl ether of dioxinone derivative was studied. The planned reaction proved feasible by heating of the substrate in toluene or xylene, giving the corresponding allene derivatives in moderate to high yield. In second, reaction of allenes and nitrones were studied. Upon heating of the allenes with nitrones underwent unusual homolytic N-O bond cleavage followed by recombination of resulting radicals to form a C-C bond, affording the corresponding lactams albeit in low yields. This research has been also studied intramolecular redox reaction of naphthoquinone derivatives, enabling construction of a new heterocyclic ring, typically furan ring skeletons. This method would serve as an efficient way to synthesize various polycyclic compounds.
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Studies on the Synthesis of Highly Oxidized Complex Natural Products of Biological Significance
Grant number：23000006 2011 - 2015
Japan Society for the Promotion of Science Grants-in-Aid for Scientific Research Grant-in-Aid for Specially Promoted Research
SUZUKI Keisuke, OHMORI Ken, ANDO Yoshio, TAKIKAWA Hiroshi, TAKAHASHI Haruko, MATSUMOTO Takashi, KUSUMI Takenori
Grant amount：\433940000 （ Direct Cost: \333800000 、 Indirect Cost：\100140000 ）
The project has dealt with the total synthesis of highly oxidized complex natural products, including (1) polyketides, (2) polyphenols, and (3) glycoconjugates with polycyclic structures. Subject 1 exploited isoxazole as a platform for stereo-controlled dimerization of anthraquinone and installation of angular cis-diol, enabling total syntheses of BE-43472B, pleospdione, and tetracenomycin C. Study on the pyranonaphthoquinone dimers led to the development of unusual dimerization protocols, enabling the first total synthesis of actinorhodin and a promising access to naphthocylines via thiolate-mediated dimerization protocol. Subject 2 was associated with synthesis of the catechin oligomers. Based on the concept of catechin–sugar analogy as well as the orthogonal activation, effective approaches have been established for synthesizing the linear as well as doubly-connected oligomers. Subject 3 dealt with the synthesis of bis-aryl C-glycoside antibiotics, and the first total synthesis of saptomycin B has been accomplished, enabling assignment of the C14-stereochmistry.
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多環式構造をモチーフとする有機化合物の合成研究
Grant number：22245012 2010 - 2012
日本学術振興会 科学研究費助成事業 基盤研究(A)
鈴木 啓介
Grant amount：\36400000 （ Direct Cost: \28000000 、 Indirect Cost：\8400000 ）
1.ポリケチド様多環性化合物の合成研究
天然由来の多環式化合物には、その生合成経路において多環芳香族骨格の一部が"脱芳香化"されることにより、高度に官能基化された構造を有するものがある。これらの合成におけるポイントは、芳香族と非芳香族とが混在するこの複雑な多環構造を、芳香化を回避しながら構築することである。そこで、部分的に脱芳香化された多環式構造を有する標的化合物を合成する上での新しい方法論の確立が望まれている。
本年度の研究においては、こうした化合物の合成を可能とする、1)ベンザインの[2+2]付加環化反応とピナコール生成反応とを基盤とする連続型多環形成法、および2)ニトリルオキシドの縮合環化反応とベンゾイン生成法について集中的に検討し、実際にこれらの方法を駆使し、セラガキノンAの初の全合成を達成した。
2.多環系複合糖質の合成研究
標記化合物群の一種であるプルラマイシン類は、強い抗腫瘍活性を持つことから、新規抗癌剤の候補として期待されている。しかし、これらの化合物群はビス-C-グリコシド構造の構築という困難な合成化学的問題により、未だその全合成は達成されておらず、その興味深い生理活性にも関わらず、研究の進捗が阻まれている。本年度の研究においては、これらビス-C-グリコシド型天然物の効率的合成に向けた基盤研究を推進した。その結果、合成目標となる天然物の母核部分として利用できる三環式化合物に対する効率的ビス-C-グリコシド化法を見出すことができた。 -
生理活性カテキンオリゴマー、ヘテロオリゴマーの選択的合成戦略に関する研究
Grant number：10F00708 2010 - 2011
日本学術振興会 科学研究費助成事業 特別研究員奨励費
鈴木 啓介, STADLBAUER Sven
Grant amount：\1800000 （ Direct Cost: \1800000 ）
植物中に多く含まれるカテキンオリゴマーは、抗菌および抗腫瘍性をはじめとする各種の興味深い生理作用を示すことから、最近注目されている。しかし、天然から純度の高い標品を入手することは一般に難しく、これが関連する領域の研究の進展を妨げている。本研究においては、合成により純粋な化合物を得るための方法論開拓を行った。
本年度の研究においては、ヘテロオリゴマーの構成ユニットとなる各種のカテキンモノマーの合成法の開拓を行った。検討の結果、A環ユニットとB環ユニットを炭素-炭素を介して結合させた後、分子内芳香族求核置換反応によりC-O結合を形成させることにより、フラバン骨格を構築する方法を見出した。この方法は、これまでの合成経路に比べ格段に効率性に優れる。実際に、この方法を用いエピアフゼレキン、エピカテキン、およびエピガロカテキンの簡便且つ選択的な合成に成功した。このように、保護基が適当に区別されたカテキンモノマーを自在に調製可能となったので、次に調製したカテキンモノマーを用い、その選択的オリゴマー化を検討した。その結果、望みの位置の保護基を選択的に除去したフェノール誘導体を用いると、従来制御困難であったフラバン骨格4,6-位間での結合形成が可能となった。現在生成物の詳細な構造を解析中である。
以上、これまでの本研究により、カテキンモノマーの効率的な合成法を見出すことができた。また、カテキンオリゴマーの合成も検討し、これまで困難であった異常な結合様式を有するカテキン二量体の合成にも成功した。 -
アトロプ異性体の新規不斉合成法の研究:キラルなビアリール型フェノール類の動力学的分割
Grant number：01F00248 2002 - 2003
日本学術振興会 科学研究費助成事業 特別研究員奨励費
鈴木 啓介, BODE Jeffrey W., BODE Jeffery
Grant amount：\2700000 （ Direct Cost: \2700000 ）
天然有機化合物に共通する多環式構造は、総じてポリケチド生合成経路に由来すると見なすことができる。言い換えれば、こうした多様なポリケチド構造の共通前駆体を何らかの方法で合成できれば、天然物に限らず、有用化合物の創出に向けた道が開けるものと期待される。
本年度の研究ではニトリルオキシドと1,3-ジケトンとの縮合環化反応を開発した。すなわち、ニトリルオキシドの前駆体となるクロロオキシムに対し、アミン塩基あるいはアルコキシドの存在下で1,3-ジケトンと反応させると、対応する縮合環化生成物が高収率で得られることを見出した。興味深いことに、両オルト位が置換されたベンズアルデヒドのクロロオキシムは不安定であり、むしろニトリルオキシドが安定に単離されることが分った。この化合物も同様な縮合環化反応を起こし、イソオキサゾールを与えることを明らかにした。この環化体は種々の変換に供せるため、ポリケチド合成単位として合成的に大きな有用性が期待できる。実際、これを利用し、イソプレンとポリケチドとのハイブリッド構造を有する天然物の構造確定に合成的に寄与することができた。さらに、多環式骨格の構築に関しては、チアゾリウム塩を触媒とするベンゾイン生成反応の有用性が明らかになってきた。さらに最近では、このベンゾイン生成反応に光学活性触媒を用いると、高いエナンチオ選択性で目的物が得られることも分った。以上の反応はいわゆる有機分子触媒を用いたものである。 -
Synthetic Study of Antibiotic Aquayamycin, Biologically Active Sugar-Aromatic Hybrid
Grant number：12640513 2000 - 2002
Japan Society for the Promotion of Science Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (C)
MATSUMOTO Takashi, SUZUKI Keisuke
Grant amount：\3400000 （ Direct Cost: \3400000 ）
Synthetic study of aquayamycin, an antibiotic which exhibits the hybid structure composed of sugar moiety and aromatic chromophore, was executed with the aim at exploring new direction of carbohydrate synthesis and aromatic synthesis.
In the early stage of the program, we focused on pioneering the first generation route to aquayamycin. The O→C-glycoside rearrangement and the [2+2] cycloaddition of benzyne and ketene silyl acetal, both of which were originally developed by us, were successfully applied for synthesizing the AB ring fragment, i.e. a 3-(phenylsulfonyl)phthalide possessing the C-olivoside. The CD ring fragment, a highly oxygen-functionalized chiral cyclohexene, was synthesized in an enantiomerically pure form via the lipase-promoted asymmetric desymmetrization of cyclohexane-1,2,3-triol derivative as a key step. These two fragments were condensed by the Hauser's method to give the highly substituted 1-anthrone derivative possessing the C-olivoside moiety. Cyclization by pinacol coupling between the C(1) carbonyl of this anthrone and the aldehyde moiety on the side chain furnished the carved tetracyclic framework of the target molecule, and final functional group interconversions led to the accomplishment of the first total synthesis of aquayamycin.
Further detailed studies ultimately shortened and revised the synthetic routes so as to render a multi-gram synthesis of each fragment.
For the purpose of application to the synthesis of physiologically useful analogue, we also examined to develop new efficient promoter of C-glycosidation of amino sugar.
Another significant finding was that scandium(III) triflate efficiently promotes aryl C-glycosidation of amino sugar derivatives, opening an opportunity of synthesizing physiologically useful analogues. -
多環芳香族系抗生物質の合成研究
Grant number：00F00759 2000 - 2002
日本学術振興会 科学研究費助成事業 特別研究員奨励費
鈴木 啓介, LUKAS Hintermann, HINTERMANN L.
Grant amount：\2400000 （ Direct Cost: \2400000 ）
FD-594は、Streptomyces sp.TA-0256より単離された多環芳香族系抗生物質であり、グラム陽性菌や腫瘍細胞に対して活性を示す。その構造は、ピラノナフトキサントン骨格を母核として、それに糖が結合している。本研究では、FD-594の全合成研究を行った。
FD-594の合成上の課題は、1)多くの官能基を持つ六環式アグリコン部分の合成、2)C3、C6、C7位に存在する不斉中心の立体選択的構築、3)高度にデオキシ化された三糖の立体選択的導入、の3点である。
今年度の研究では、このうちの一つ目の課題について詳細な検討を行った結果、重要な鍵中間体であるAB環に相当するヨードフェノールの合成とDEF環に相当するキサントン骨格を持つカルボン酸の合成に成功した。すなわち、AB環に相当するヨードフェノールは、容易に調製可能な4-メチルサリチル酸誘導体を原料として用い、数工程を経てアミドへと誘導後、オルト位の位置選択的なリチオ化、それに引き続くプロピルオキシランとの反応を経ることによって合成した。
一方、DEF環に相当するキサントン骨格を持つカルボン酸は、セサモール誘導体のリチオ化体とジメチルスクシニルスクシネートから誘導したベンズアルデヒドを結合させた後、分子内芳香族求核置換反応を経ることによって合成した。
さらに、これらの両部分を縮合させ、得られたエステルのパラジウム環化反応を試みた結果、FD-594のアグリコン前駆体に相当するオルト四置換のビアリールラクトンを得ることができた。 -
1999 - 2004
科学技術振興機構 戦略的な研究開発の推進 戦略的創造研究推進事業 CREST
鈴木 啓介
Authorship：Principal investigator
天然の生理活性分子にはハイブリッド構造を有するものがあります。こうした分子の活性は、その構造ならではのものであることがしばしばあります。一方、このような分子の合成は、既存の方法を単なる組み合わせでは達成できないことも多く、関連領域の進歩の妨げとなっています。この観点から本研究では主に(1)芳香族、(2)糖、(3)ヘテロ原子の三要素を含む複合分子をとりあげ、高効率合成法の開拓を研究します。
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Synthetic Study of Pradimicns, Antiviral Antibiotics Possessing the Binding Abilities to Oligosacchrides
Grant number：10440214 1998 - 1999
Japan Society for the Promotion of Science Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (B)
SUZUKI Keisuke, OHMORI Ken, MATSUMOTO Takashi
Grant amount：\13400000 （ Direct Cost: \13400000 ）
The pradimicin-benanomicin antibiotics constitute a new class of natural products with a benzo[a]naphthacenequinone core wkh an amino acid and a disaccharide.They show anti-fungal and anti-HIV activities, which are related to the selective binding abilities to mannose-rich oligosaccharides, e.g. the mannane surface of fungi or gp 120 of HIV. The unique structure as well as the significant biological activities led me to undertake the synthesis of this class of compounds.
The most intriguing challenge among the synthetic issues is the control of the vicinal diol stereogenicities at the corner of the pentacyclic skeleton comprises, to which we explored the possible use of intramolecular pinacol coupling of bis-aldehyde. Along these lines, we found that this reaction is useful for the above issue.
The SmIィイD22ィエD2-mediated pinacol coupling of biphenyl o, o'-dialdehyde was found to proceed stereo selectivelly and gave only trans diol, which enabled us to achieve the synthesis of the trans diol structure of B ring as diastereomerically pure form. Furthermore, the reaction proved to proceed stereospecifically, thereby enabling the full transmission of the axial chirality into the two central chiralities. Thus, we studied the stereoselective and -specific pinacol coupling of bis-aldehyde, providing the requisite trans-diol in enantio- and diastereomerically pure form, which served as a basic strategy for the total synthesis of the pradimicin-benanomicin class antibiotics.
Total synthesis of the pradimicinone (benanomicinone), the common aglycon of the class of natural products, based on the above mentioned pinacol cyclization, has been achieved. -
Development of viable synthetic route to the furaquinocins and its application to creating new antitumor agents
Grant number：09554045 1997 - 1999
Japan Society for the Promotion of Science Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (B)
SUZUKI Keisuke, FUJIMOTO Katsumi, OHMORI Ken, MATSUMOTO Takashi
Grant amount：\10200000 （ Direct Cost: \10200000 ）
An efficient and flexible synthetic route to the furaquinocins, a new class of antibiotics which show cytotoxic activity against HeLa S3 and B16 melanoma cells but no antimicrobial activity, was developed. These compounds pose new synthetic challenges due to their unique hybrid structure composed of the polyketide-derived naphthoquinone and the isoprenoid side chain, including (1) stereocontrol of three contiguous stereogenic centers at C-2, C-3 (quaternary), and C-10, (2) selective construction of the densely functionalized naphthoquinone, and (3) establishment of the sterically congested aromatic-isoprenoid hybrid structure.
Stereocontrolled construction of two of the three contiguous stereogenic centers, including a quaternary chiral center, was effected by the 1,2-rearrangement of optically active epoxy alcohol armed with the cobalt-complexed alkyne as the migrating group. The alkyne in the resulting homopropargyl alcohol, after decoordination of the cobalt, effectively worked as the C2 unit for constructing the naphthofuran skeleton by an electrocyclic benzannulation. The third chiral center was constructed by stereoselective methylenation of the aldehyde, adjacent to the quaternary chiral center, by a sulfur ylide. Through the resulting epoxide as the common intermediate, total syntheses of furaquinocin D, furaquinocin A, furaquinocin B, and furaquinocin H were achieved in a convergent manner.
Biological activity test revealed that some of the synthetic intermediates exhibit potent cyctocidal activities comparable to natural furaquinocins, which provides a valuable information for designing new synthetic antitumor agents. -
Exploration of Practical Synthetic Tolls for Molecular Construction
Grant number：08245102 1996 - 1998
Japan Society for the Promotion of Science Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research on Priority Areas
KUWAJIMA Isao, SUZUKI Keisuke, NARASAKA Koichi, ITO Yoshihiko
Grant amount：\29300000 （ Direct Cost: \29300000 ）
Purpose : Exploration of Useful Methodologies and Synthesis of Complex Natural Products
Members : 1996, 8 (for Appraisal) and 73 (for Research)
1997, 8 (for Appraisal) and 78 (for Research)
1998, 8 (for Appraisal) and 75 (for Research)
Meetings : 1st Symposium : January 13-14, 1997 (Kyoto)
2nd Symposium : June 12-13, 1997 (Tokyo)
3rd Symposium : December 8-9, 1997 (Osaka)
4th Symposium : May 21-22, 1998 (Sendai)
5th Symposium : December 14-15, 1998 (Tokyo)
6th Symposium : July 2, 1999 (Tokyo)
Publications : Research Abstracts of Every Member in 1996
Research Abstracts of Every Member in 1997
Research Abstracts of Every Member in 1998
Research Abstracts of Every Member in 1999
Total syntheses of a lot of celebrated natural products such as taxol, radicsicol, rabidomycin, polycavernoside A, madindoline, zaragozic acid A, antillatoxin, fredericamycin, terpestacin, streptovaricin U and so on, have been achieved. For construction of organic molecule, several useful methodologies have been developed for selective construction of heterocycles containing nitrogen, cyclic poly ether structures, acyclic polyols, and asymmetric construction quaternary carbon useful for the syntheses of complex natural products -
Total Synthesis of Complex Natural Products
Grant number：08245103 1996 - 1998
Japan Society for the Promotion of Science Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research on Priority Areas
KUWAJIMA Isao, KOBAYASHI Susumu, KITAHARA Takeshi, OHFUNE Yasufumi, MURAI Akio, SUZUKI Keisuke
Grant amount：\131800000 （ Direct Cost: \131800000 ）
Total syntheses of complex natural products have been studied in this research group. During this investigation, taxane diterpene was one of major synthetic targets, and enantioselective total syntheses of (+)-taxusin and (-)-taxol have been efficiently achieved based on the B ring cyclization methodology of AC fragment.
Other representative natural products synthesized during this research period are radicicol, pironectin, tanabalin, furaquinocine, and polycavernoside.
Synthtic studies on α,α-disubstituted α-amino acid sub-structure, zoanthamine/nor-zoanthamine alkaloids, and ravidomycin were also developed. -
メタロクライゼン転位反応による新規遠隔不斉誘起反応の開発
Grant number：08640697 1996
日本学術振興会 科学研究費助成事業 基盤研究(C)
松本 隆司, 鈴木 啓介
Grant amount：\2500000 （ Direct Cost: \2500000 ）
ある不斉点から隔たる位置に不斉を誘起する遠隔不斉誘起は、鎖状立体制御法の急速な進展にもかかわらず、未だチャレンジングな課題として、さまざまな試みが行われている状況にある。本研究では、アレンのヒドロジルコニウム化により発生するアリルジルコニウムと、やはりヒドロジルコニウム化によりアルキンより発生できるビニルジルコニウムを用いるone-potでのメタロクライゼン転位反応を基盤とし、新しい遠隔不斉誘起法の開発を試みた。
光学活性な4-メチル-1,2-ベンタジエン-5-オールをモデルとし、その水酸基をさまざまな保護基で保護した化合物を合成して、それらのヒドロジルコニウム化により発生させたアリルジルコニウムのメタロクライゼン転位反応を試た。その結果、二塩化亜鉛の存在下で種々のビニルジルコニウムに対して、速やかにメタロクライゼン転位型のカップリング反応が進行し、アリルジルコニウムのα位、ビニルジルコニウムのβ位で炭素-炭素結合を形成した生成物を選択的に高収率で得ることができた。この際、上述の保護基として金属イオンに対する配位性の高いメトキシメチル基などを用いると、高度な1,5-不斉誘起が起こることが明らかになった。ジアステレオマ-生成比はカップリングするビニルジルコニウムひいてはルキンの構造に依存し変化するものの、試た限りでは6:1から28:1と1,5-不斉誘起としては異例に高い選択性が実現できる。また、この選択性と生成する二重結合の幾何異性体比には相関性があり、生成する二重結合のZ体選択性が高い程、遠隔不斉誘起の選択性も高い。このことは反応の詳細なメカニズム、立体経路を明らかにしていく上で興味深い知見である。 -
ベンザインとオレフィンの[2+2]環付加反応に関する研究
Grant number：07640730 1995
日本学術振興会 科学研究費助成事業 一般研究(C)
鈴木 啓介
Grant amount：\2200000 （ Direct Cost: \2200000 ）
高反応性化学種であるベンザインは異例に低いLUMOを有するため、基底状態でオレフィンとの[2+2]環付加反応を起こす点に大きな特徴がある。しかし、この反応は、従来精密合成化学にはほとんど利用されてこなかった。これは、おそらく、従来、十分効率的なベンザインの発生法がなかったこと、さらには、パートナーとなるオレフィンの選択が適切でなかったことに起因するものであるものと考えられる。
一方、先に我々はo-ハロアリール=トリフラートの還元的脱離を利用すれば、低温で速やかにベンザイン種を定量的に発生できることを見出した。本研究では、ベンザインと電子豊富オレフィンとの[2+2]の環付加反応に焦点をあて、その実行可能性、位置選択性について検討を加えた。その結果、オレフィン成分としてケテンシリルアセタールが特に優れた反応性を示し、低温下速やかに収率よく環付加物を与えることを見出した。また、αアルコキシベンザイとの反応は位置選択性良く、head-to-head型の環付加物のみが得られることが分った。こうして得られる各種環付加物を加水分解し、合成的に様々な有用性が期待される種々のベンゾシクロブテノン誘導体が高収率で得られることを明らかにした。この成果は、生理活性物質の合成と関連して、その選択的合成法の開発への期待が高まっている芳香族関連化合物に大きな寄与をするものと考えられるので、今後その点について検討を加えて行きたい。 -
隣接基関与をモチーフとする新しい選択的有機合成の研究
Grant number：06640699 1994
日本学術振興会 科学研究費助成事業 一般研究(C)
鈴木 啓介
Grant amount：\2000000 （ Direct Cost: \2000000 ）
隣接基関与の概念は、特定の有機分子の異常な反応性や選択性の説明に援用されてきたが、有機合成反応の合理的設計のためのガイドラインとして合目的的用いられた例はほとんどない。本研究は、この効果を拡張した形で捕らえ直し、それをモチーフとして選択的有機合成反応の設計、開発を行うことを目的として行ったものである。その結果、以下の2項目について、有用な知見を得ることができた。
アセチレン-コバルト錯体はそのα位のカチオンを強力に安定化する効果を持つ。この点に着目して、2-プロペンの2位にアルキン-コバルト錯体を導入したところ、予期したとおり、求核的な反応性の高いオレフィンとして挙動を示すことが分った。すなわち、ルイス酸条件のカルボニル-エン反応における良好なエン供与体となる他、分子内にあっては脱離基の反応性を上げる隣接基としてのふるまいを見せる。反応の立体経路を明らかにすべく、さらに検討を加えている。
一方,天然有機化合物の中には、特異なシクロプロパン構造を有するものがあり、特異な生理活性と相俟って注目を集めている。これらの化合物の生合成では、ホモアリル型の隣接基関与に始まるシクロプロパン形成が含まれていることが多く、その観点から本研究では"生合成類似経路"による含シクロプロパン天然有機化合物の合成を検討した。その結果、ホモアリル型型骨格転位を制御できる反応基質の設計に成功し、立体選択性を含め、新たな特徴を有する合成反応として確立することができた。今後さらに、天然物合成への展開を図りたいと考えている。 -
Typical Metal-Catalyzed Asymmetric Synthesis
Grant number：05234105 1993 - 1995
Japan Society for the Promotion of Science Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research on Priority Areas
YAMAMOTO Hisashi, NAKAI Takeshi, TAMAO Kouhei, SUZUKI Keisuke, SHIOIRI Takayuki, OGUNI Nobuki
Grant amount：\95500000 （ Direct Cost: \95500000 ）
Asymmetric synthesis has developed rapidly and extensively, and is now growing into a new way of producing optically active chiral compounds that is more general and efficient than enzymatic reactions in many cases. The aim of project "typical metal-catalyzed asymmetric synthesis, " was executed by many organic chemists diving into six research groups of "development and application of designer Lewis acid (Yamamoto), " "asymmetric reactions of diketene with aldehydes catalyzed by chiral Schiff base-titanium complexes (Oguni), " "asymmetric synthesis utilizing chiral quaternary salt catalysts and chiral auxiliaries from monoterpenes (Shioiri), " "some new ways of organometallicbased stereocontrol (Suzuki), " "asymmetric intramolecular hydrosilation (Tamao), " and "development of catalytic asymmetric reactions (Nakai)" for three years beginning in 1993. This project was not only create various new asymmetric reactions by taking advantage of characteristics of typical elements, but also to apply many enantio- and diastereoselective reactions to the synthesis of the complex multi-chiral compounds including useful natural products. During 1993-1995, many new asymmetric or stereoselective reactions related to Diels-Alder reaction (Yamamoto), protonation (Yamamoto), addition-ring opening reaction of diketenes with aldehydes (Oguni), aldol reaction (Shioiri), addition of silylacetylenes to carbonyl compounds (Shioiri), 1,2-rearrangement of alkynyl groups (Suzuki), metallo-ene reaction (Suzuki), intramolecular hydrosilation (Tamao), addition of aldehydes with diethylzinc (Nakai), and allylation (Nakai) were developed.
-
生体触媒を利用したシアリル糖鎖誘導体のハイブリッド合成
Grant number：05274224 1993
日本学術振興会 科学研究費助成事業 重点領域研究
須貝 威, 松本 隆司, 鈴木 啓介, 太田 博道
Grant amount：\2100000 （ Direct Cost: \2100000 ）
酵素法を利用したシアル酸誘導体の大量合成法:シアル酸は、N-アセチルマンノサミンとピルビン酸から酵素的に合成可能である。酵素法の問題点の1つである大過剰のピルビン酸の除去について検討した。その結果、ピルビン酸デカルボキシラーゼが問題解決の有効な手段となることを見い出した。この方法は大量スケールで容易に実施可能である。現在、効率のよいデカルボキシラーゼ生産菌をスクリーニングしており、未同定細菌や酵母の一種を見い出している。KDN関連化合物合成への応用を検討中である。
2.3-デオキシ-D-マノン-2-オクチュロソン酸(KDO)アルドラーゼの合成化学的利用:土壌サンプルをスクリーニングすることにより、グラム陽性菌の一種、Aureobacterium barkeri KDO-37-2株から新規KDOアルドラーゼ(EC4.1.2.23)を得た。このものの基質特異性、反応の立体化学を検討し、新規含フッ素アナログの合成に成功した。なお、この研究は、米国Scripps研究所C.-H.Wong教授との共同研究である。
3.糖脂質合成に有用な長鎖光学活性beta-ヒドロキシ酸誘導体の合成:従来光学分割に多大の労力を費やしていた長鎖光学活性beta-ヒロドキシ酸およびフッ素アナログを、簡便に調製することに成功した。リパーゼや酵母の一種Saccharomyces cerevisiae、Pichia farinosaなどの生体触媒を用いることによって不斉炭素を導入し、さらに有機合成によって必要な炭素骨格を構築した。 -
有機合成に役立つ新しいカチオン活性種の選択的発生と捕捉に関する基礎的研究
Grant number：04640514 1992
日本学術振興会 科学研究費助成事業 一般研究(C)
鈴木 啓介, 松本 隆司
Grant amount：\2000000 （ Direct Cost: \2000000 ）
1-アルキンのヒドロジルコニウム化で得られるアルケニルジルコノセン錯体は、従来、求核性に乏しく、カルボニル化合物との反応は極めて遅いとされてきた。しかし、この反応を触媒量の過塩素酸銀の存在下で行うと、著しく付加速度が速くなり、高収率で対応する付加体を与えることが分った。わずか1モル%程度の銀塩で十分な加速が起こる。発生するカチオン型錯体がカルボニル基の効果的に活性化するためと考えられる。なお、この加速効果は、対応するアルキル錯体にも見られた。この反応をプロパルギルシランに適用すると、付加に続き1、4脱離が起こり、共役ジエンを与える。1、4脱離の段階でも過塩素酸塩の存在が必要である。さらに、市販のアルコキシアセチレン類にこの反応を適用すると、アルデヒドの2炭素、4炭素ホモロゲーションが容易に行えることも分った。
さらに、NbCl_5がルイス酸として極めて特異な反応性を示すことが分った。すなわち、NbCl_5の在存下ではアリルシランとアルデヒドとが2:1の化学量論で反応し、シクロプロパン体を与えた。この異常反応は、(1)1当量目の付加に続いて、ニオブの高い酸素親和性によりニオブオキシドの脱離とホモアリル型の隣接基関与が起こる、(2)カチオニックな化学種の異性化が起こった後、最も寄与の大きい2級のシクロプロピルカルビニル種で2当量目のアリルシランの捕捉が起きる、という経路によることが分った。この反応はシクロプロパンのα位の強力なカチオン安定化効果を如実に示したものと言える。
さらにこの知見を合成的に生かすことを検討した結果、ビニルシクロプロパンがカルボニル-エン反応において極めて高い反応性を有することを明らかにし、さらに新しいシクロブタン、シクロブテンの合成法を確立することに成功した。 -
前周期遷移金属錯体を複合的に用いる新しい反応試剤の開発
Grant number：03215229 1991
日本学術振興会 科学研究費助成事業 重点領域研究
鈴木 啓介, 松本 隆司
Grant amount：\2500000 （ Direct Cost: \2500000 ）
カチオン錯体の示す、ルイス酸としての独特の反応性に着目し検討を加えた。すなわち、アセチレンのヒドロジルコニウム化反応によって得られるアルケニルジルコニウムは、カルボニル基に対する付加反応性に乏しい。しかし、過塩素酸銀(触媒量)により反応は著しく促進され、高収率でアルケニル化体を与えることを見出した。発生するカオチン型錯体による効果的なカルボニルの活性化が起きるためと考えられる。この効果は、オレフィンより調製したアルキル錯体でも見られる。この反応形成をプロパルギルシランに適用すると、付加に続いて1、4ー脱離により、ジエンを与えた。さらに離囲を拡大し検討を加えた結果、NbCl_5がルイス酸として特異な反応性を示すことを見出した。例えば、桜井反応では、1当量目のアリルシランの付加に続き、ニオブアルコキシドの脱離とホモアリル型の隣接基関与により、最も安定なカオチン種が2当量目のアリルシランによる捕捉が起き、シクロプロパンを含む2重付加生成物を与えた。さらに、2級ホスフィンのカルボニル化合物への付加反応でも、最初の単純な付加に続く分子内酸化還元過鍋をNbCl_5が特異的に触媒することが分った。
一方天然物合成への応用としてアリ-ルCーグリコシド系抗生物質の合成研究を行った。この種の化合物は、その構造のみならず、抗腫瘍性など生理活性的にも注目されている。ここで、合成上の最大のポイントであるCーアリ-ルグリコシド結合の形成に新たなアプロ-チを開発した。すなわち、ルイス酸条件下、フッ化糖と遊離のフェノ-ルとの反応を行うと、低温で速やかにOーグリコシド化が起こる。続いて、徐々に、昇温するとOーグリコシドからCーグリコシドへの変換が起き、フェノ-ル性水酸基のオルト位に選択的にCーグリコシド結合が形成される。この反応は、通常のルイス酸でも進行するが、収率、選択性などの点でCp_2HfCl_2とAgClO_4との複合系がはるかに優れていることが分った。この反応を利用して、ビネオマイシノンB_2およびギルボカルシンMの全合成を行うことに成功した。 -
前周期遷移金属錯体を複合的に用いる新しい反応試剤の開発
Grant number：02231228 1989 - 1991
日本学術振興会 科学研究費助成事業 重点領域研究
鈴木 啓介, 松本 隆司
Grant amount：\2600000 （ Direct Cost: \2600000 ）
有機金属試剤の複合利用による新機能の発現と、それを用いる新しい有用な合成反応の開発の研究を行っている。本年度は特に次の二点について重点的な研究を行った。
1.Cp_2MCl_2ーAgX(M=Zr,Hf)系によるCーアル-ルグルコシド化反応
最近我々が見出した新しい手法のうち、「O→Cーグルコシド転位反応」を用いた抗腫瘍抗体物質ビネオマイシンB_2の全合成を計画し、それに適用すべく、試剤の洗練化、より詳細な検討を行った。メタロセンの中心金属や銀塩の選択、複合比の調節、グリコシル供与体の設計などにより、目的に応じた反応性の発現が可能であることが明らかになった。これを基に(1)多環性フェノ-ル類との位置選択的反応,(2)アノマ-間の平衡を利用した、熱力学的支配による2ーデオキシ糖の反応の立体化学の制御、が可能になり、ビネオマイシノンB_2の全合成に成功した。
2.新しい炭素ー炭素結合形成反応の開発
五塩化ニオブーアリルトリメチルシラン複合系による新しい形式の炭素ー炭素結合形成反応を見出した。
アルデヒドとアリルトリメチルシランに対して、五塩化ニオブを活性化剤として作用させると、通常の桜井型反応に引き続き、もう1モルのアリルトリメチルシランが反応し、シクロプロピル基の形成を伴いながらアリル化が進行する。この反応はホモアリルアルコ-ルの水酸基が五塩化ニオブの作用で脱離することにより生成するカチオン中間体を経由しているものと考えられ、その独特な活性化様式に興味が持たれる。 -
前周期遷移金属錯体を複合的に用いる新しい反応試剤の開発
Grant number：01649519 1989
日本学術振興会 科学研究費助成事業 重点領域研究
鈴木 啓介
Grant amount：\2000000 （ Direct Cost: \2000000 ）
先に我々は、4族元素の二塩化メタロセン錯体と過塩素酸銀との組合わせがフッ化グリコシルを極めて強く活性化する能力を有することを見いだした。今年度は、この優れたクリコシド活性化法を背景として糖質合成の新しい可能性を探るとともに、試薬の複合化による高次機能の発現の可能性をより一般的に検討した。
最近、ビネオマイシンやラビドマイシンの様に、特異な芳香環部分と糖質部分とが炭素-炭素結合で結合した新しい化合物が単離され、その新規な構造から、また抗腫瘍性を示すことから注目されている。合成化学的にはC-アリ-ルグリコシド結合の形成が要点である。これに対し、先のグリコシド活性化法の適用を検討した結果、糖質と芳香環との結合に関する二つの方法を開発した。方法Iは、フリ-デル・クラフツ型の芳香族置換によるものである。Cp_2ZrCl_2とAgClO_4の複合系が特に効果的で、糖と芳香環との結合が従来法に比べて、格段に速やかに、高収率で行える。この反応の立体、並びに位置選択性を明らかにした。方法IIは新反応である。ルイス酸条件下、フッ化糖とフェノ-ル類との反応を行うと、低温でO-グリコシド化が起こる。昇温するとそれがC-グリコシドへ転位し、位置選択的にC-アリ-ルグリコシド結合が生成する。反応は通常のルイス酸でも進行するが、Cp_2HfCl_2とAgClO_4の複合系が様々な点で優れている。応用として、ビネオマイシンB_2のC-アリ-ルグリコシド部分を合成したほか、O-グリコシド形成についても基礎的なデ-タを集積した。
活性化機構に関してはカチオン錯体におけるフッ化物イオンとの高い親和性を想定している。この観点から種々検討の結果、二塩化メタロセンと過塩素酸銀のモル比を従来の1:1にかえ、1:2とした場合にさらに高い反応性が得られることが分った。