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(In Japanese)ハイブリッド型生理活性分子の高効率構築法の開発

Research report code R000000235
Posted date Sep 30, 2002
  • (In Japanese)鈴木 啓介
  • (In Japanese)東京工業大学大学院理工学研究科
Research organization
  • (In Japanese)東京工業大学院理工学研究科
Report name (In Japanese)ハイブリッド型生理活性分子の高効率構築法の開発
Technology summary (In Japanese)天然由来の生理活性物質の中にはハイブリッド構造を持つものが多く見られ,それらの生理活性はその特有な複合構造に由来するものが多い。本研究はハイブリッド型化合物の合成を大目標とし,具体的目標として芳香族-糖-ヘテロ原子の酸要素から成る複合型分子を取り扱う。芳香族およびアミノ糖の構成要素から成る点で共通した二つの標的分子,ラビドマイシン(抗腫瘍性抗生物質)ならびにプラジミシン(抗ウイルス性抗生物質)の合成研究を行った。これに関連して,特にヘテロ原子の存在下でも通用する合成反応の開拓を目指し,ベンゾシクロブテン誘導体に潜在する種々の反応性を活かした多環式芳香族化合物や脂環式化合物の合成法を検討した。
Research field
  • Synthesis of antibiotics
  • Clinical application of antibiotics acting on pathogenic organisms
  • Basic research of antitumor (=antineoplastic) antibiotics
Published papers related (In Japanese)(1)S. Futagami, Y. Ohashi, K. Imura, T. Hosoya, K. Ohmori, T. Matsumoto, and K. Suzuki, Total Synthesis of Ravidomycin: Revision of Absolute and Relative Stereochemistry, Tetrahedron Lett., 41, 1063-1067 (2000).
(2)T. Hosoya, T. Hamura, Y. Kuriyama, M. Miyamoto, T. Matsumoto, and K. Suzuki, Silicon-Directed Regioselective [2+2] Cycloaddition of α-Alkoxybenzyne and Ketene Silyl Acetals, Synlett, 2000, 520-522.
(3)S. Yamanoi, T. Matsumoto, and K. Suzuki, Reaction of 1-Iodoalkynes with Allylzirconiums: Generation of Alkylidene Carbenoid via Allylmetallation, Tetrahedron Lett., 40, 2793-2796 (1999).
(4)K. Ohmori, M. Kitamura, and K. Suzuki, From Axial Chirality to Central Chiralities: Pinacol Cyclization of 2,2'-Biaryldicarbaldehyde en route to trans-9,10-Dihydrophenathren-9,10-diol Substructure of Pradimicin-Benanomicin Antibiotics, Angew. Chem., Int. Ed., Engl., 38, 1226-1229 (1999).
(5)M. Kitamura, K. Ohmori, T. Kawase, and K. Suzuki, Total Synthesis of Pradimicinone, the Common Aglycon of the Pradimicin-Benanomicin Antibiotics, Angew. Chem., Int. Ed., Engl., 38, 1229-1232 (1999).
(6)M. Kitamura, K. Ohmori, and K. Suzuki, Divergent Behavior of Cobalt-Complexed Enynyl Compounds Having a Leaving Group, Tetrahedron Lett., 40, 4563-4566 (1999).
(7)S. Yamanoi, H. Ohrui, K. Seki, T. Matsumoto, and K. Suzuki, Alkylzirconation of 1-Alkynes Catalyzed by Triphenylcarbenium Tetrakis(pentafluoro)borate, Tetrahedron Lett., 40, 8407-8410 (1999).
(8)Thermodynamic and Kinetic Properties of trans-3, 4, 5,.6-Tetramethyl-9, 10-dihydroxy-9, 10-dihydrophenanthrene : Pseudo-Rotational Barriers around Biphenyl Axis, Chirality, 12, 548-550 (2000), by H.Kato, K.Ohmori, and K. Suzuki.
(9)First Total Synthesis of Astilbin, A Biologically Active Glycosyl Flavonoid isolated from Chinese Folk Medicine, Tetrahedron Lett., 41, 5537-5541 (2000), by K.Ohmori, H.Ohrui, and K. Suzuki.
(10)Glycosylation Study on Pradimicin-Benanomicin Antibiotics, Tetrahedron Lett., 41, 6827-6832 (2000), by H.Kato, K.Ohmori, and K.Suzuki.
(11)Synthetic Study of Hybrid Natural Products, Ravidomycin, Pure Appl. Chem., 1783-1786 (2000), by K.Suzuki.
(12)Synthestic Study of Aquayamycin. Part 1 : Synthesis of 3-(Phenylsulfonyl)phthalides Possessing a β-C-Olivoside, Tetrahedron Lett., 41, 8383-8387 (2000), by T.Matsumoto, H.Yamaguchi, T.Hamura, M.Tanabe, Y.Kuriyama, and K.Suzuki.
(13)Synthestic Study of Aquayamycin. Part 2 : Synthesis of the AB Ring Fragment, Tetrahedron Lett., 41, 8389-8392 (2000), by H.Yamaguchi, T.Konegawa, M.Tanabe, T.Nakamura, T.Matsumoto, and K. Suzuki.
(14)Synthestic Study of Aquayamycin. Part 3 : First Total Synthesis, Tetrahedron Lett., 41, 8393-8396 (2000), by T.Matsumoto, H.Yamaguchi, M.Tanabe, Y.Yasui, and K.Suzuki.
(15)Alkylzirconation, J.Organomet. Chem., 624, 143-150 (2001), by S.Yamanoi, K.Seki, T.Matsumoto, and K.Suzuki.
(16)Convenient Procedure for One-Pot Conversion of Azides to N- Monomethylamines, Synlett, 2001, 1003-1005, by H.Kato, K.Ohmori, and K.Suzuki.
(17)Group-selective Hydroalumination of Bis-Alkynyl Alcohols, Org. Lett., 3, 1057-1060 (2001), by K.Ohmori, T.Suzuki, K.Taya, T.Ohta, D.Tanabe, and K.Suzuki.
(18)Synthesis of (-)-Malyngolide via Group-Hydralumination of Bis-Alkynyl Alcohols, Org. Lett., 3, 1741-1744 (2001), by T.Suzuki, K.Ohmori, and K.Suzuki.
(19)Lipase-Catalyzed Asymmetrization of Diacetate of meso-2-(2-Propynyl)cyclohexane-1,2,3-triol toward the Total Synthesis of Aquayamycin, Synlett, in press, by T.Matsumoto, T.Konegawa, H.Yamaguchi, T.Nakamura, T.Sugai, and K.Suzuki.
(20)Facile and Highly Enantioselective Synthesis of Axially Chiral Biaryls by Enzymatic Desymmetrization, Synlett, in press, by T.Matsumoto, T.Konegawa, T. Nakamura, and K.Suzuki.
(21)Group-Selective Hydroalumination of Bis-Alkynyl Alcohols: Further Scope, Tetrahedron Lett., submitted, by K.Ohmori, Y.Hachisu, T.Suzuki, and K.Suzuki.
Research project
  • Core Research for Evolutional Science and Technology;Creation and Functions of New Molecules and Molecular Assemblies
Information research report
  • (In Japanese)鈴木 啓介. 電子・光子等の機能制御 ハイブリッド型生理活性分子の高効率構築法の開発. 戦略的基礎研究推進事業 平成11年度 研究年報.科学技術振興事業団, 2000. p.709 - 711.