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1995 Fiscal Year Final Research Report Summary

Structural Studies on Reactive Complexes for Highly Selective Organic Reactions

Research Project

Project/Area Number 06557117
Research Category

Grant-in-Aid for Developmental Scientific Research (B)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionUniversity of Tokyo

Principal Investigator

ODASHIMA Kazunori  University of Tokyo Faculty of Pharmaceutical Sciences, Associate Professor, 薬学部, 助教授 (30152507)

Co-Investigator(Kenkyū-buntansha) IMANARI Mamoru  JEOL Ltd.Application & Research Center General Manager, 分析技術本部, センター長
HIGUCHI Tsunehiko  University of Tokyo Faculty of Pharmaceutical Sciences, Assistant Professor, 薬学部, 助手 (50173159)
SODEOKA Mikiko  Sagami Chemical Research Center Senior Researcher, 副主任研究員 (60192142)
NOGUCHI Hiroshi  University of Shizuoka School of Pharmaceutical Sciences, Professor, 薬学部, 教授 (60126141)
ENDO Yasuyuki  University of Tokyo Faculty of Pharmaceutical Sciences, Associate Professor, 薬学部, 助教授 (80126002)
Project Period (FY) 1994 – 1995
KeywordsReactive Complex / Solution Structure / Nuclear Magnetic Resonance / Calixarene Ester / Chiral Lithium Amide / Teleocidin Analogue / Chiral Palladium Complex / Ruthenium Porphyrin
Research Abstract

Solution structures of reactive complexes for several kinds of highly selective organic reactions have been investigated in detail by multinuclear NMR spectroscopy and other methods, and the following new results have been obtained.
1.Reactive Complexes for Membrane Potential Changes Selective changes in membrane potential, observed for dopamine and related compounds by a PVC matrix liquid membrane based on calix [6] arene hexaester, have been shown by ^1H-NMR to be based on discrimination of nonpolar moieties by cavity inclusion.
2.Reactive Complexes for Promotion of Cancer Detailed ^1H-NMR investigations on the solution structures of a series of indolactams and benzolactams, synthesized as a novel type of model compounds of TPA-type cancer promoter teleocidin, have revealed their active conformation to be the twist form.
3.Reactive Complexes for Asymmetric Reaction of Lithium Enolates Detailed ^6Li-and ^<15>N-NMR investigations have revealed that the complex leading to high selectivities in asymmetric deprotonation mediated by chiral lithium amide is its 1 : 1 mixed aggregate with LiCl.
4.Reactive Complexes for Catalytic Asymmetric C-C Bond Formation Detailed ^1H-and ^<31>P-NMR investigations have revealed the solution structures of chiral BINAP-Pd complexes leading to high selectivities of catalytic asymmetric Heck and aldol reactions.
5.Reactive Complexes for Biomimetic Catalyic Oxidation The complex leading to the high efficiencies of catalytic oxidation by Ru-porphyrin complex for unreactive alkanes and aromatic compounds has been shown to be [Ru^<VI> (por) (X) (O) ]^+ (X=Cl or Br) by ^1H-NMR and other methods.

  • Research Products

    (25 results)

All Other

All Publications (25 results)

  • [Publications] K. Odashima: "Chemical Sensing Based on Membrane Potential Change Induced by Host-Guest Complexation at a Membrane Surface" Supramolecular Chemistry. 4. 101-113 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K. Yagi: "Channel Mimetic Sensing Membranes for Alkali Metal Cations Based on Oriented Monolayers of Calixarene Esters" Journal of Electroanalytical Chemistry. 401. 65-79 (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y. Endo: "Chiral Requirements for Tumor Promoters : Conformations and Activity of Benzolactams" Bioorg. Med. Chem. Lett.4. 491-494 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y. Endo: "Synthesis, Conformation, and Biological Activity of Teleocidin Mimics, Benzolactams. Structure-Activity Studies of Teleocidins." J. Am. Chem. Soc.118(in press). (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y. Kawasaki: "Identification of Adducts Formed by Reaction of Purine Bases with a Mutagenic Anthra-quinone, Lucidin : Mechanism of Mutagenicity" Dhem. Pharm. Bull.42. 1971-1973 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K. Inoue: "Spirostanol and Furostanol Glycosides of Costus speciosus (KOENIG.)SM." Natural Medicines. 49. 336-339 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K. Ohrai: "Effects of Solvents and Additives in the Asymmetric Heck Reaction of Alkenyl Triflates : Catalytic Asymmetric Synthesis of Decalins" J. Am. Chem. Soc.116. 11737-11748 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M. Sodeoka: "Catalytic Asymmetric Aldol Reaction Via Chiral Pd(II) Enolate in Wet DMF" J. Org. Chem.60. 2648-2649 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M. Komuro: "Application of Chemical Cytochrome P-450 Model Systems to studies on Drug Metabolism-VIII. Novel Metabolism, of Carboxylic Acids" Bioorg. Med. Chem.3. 55-65 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] H. Ohtake: "The Highly Efficient Oxidation of Olefins, Alcohols, Sulfides and Alkanes with Heteroaromatic N-Oxides Catalyzed by Porphyrins" Heterocyles. 40. 867-903 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K. Koga: "Approaches to Catalytic Asymmertric Formation and Reactions of Lithium Enolates" J. Synth. Org. Chem., Jpn.53. 1021-1032 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 小田嶋和徳: "膜電位変化を伴うホストーゲスト分子認識" 薬学雑誌. 115. 431-445 (1995)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K. Odashima: "Molecular Recognition : Receptors for Molecular Guests (Comprehensive Supramolecular Chemistry)" Pergamon Press (in press), (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 小田嶋和徳: "超分子化学への道" 学会出版センター, (印刷中) (1996)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] K.Odashima, R.Naganawa, H.Radecka, M.Kataoka, E.Kimura, T.Koike, K.Tohda, M.Tange, H.Furuta, J.L.Sessler, K.Yagi, and Y.Umezawa: ""Chemical Sensing Based on Membrane Potential Change Induced by Host-Guest Complexation at a Membrane Surface"" Supramol.Chem.4. 101-113 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K.Yagi, S.B.Khoo, M.Sugawara, T.Sakaki, S.Shinkai, K.Odashima, and Y.Umezawa: ""Channel Mimetic Sensing Membranes for Alkali Metal Cations Based on Oriented Monolayrs of Calixarene Esters"" J.Electroanal.Chem.401. 65-79 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Endo, M.Ohno, M.Hirano, M.Takeda, A.Itai, and K.Shudo: ""Chiral Requirements for Tumor Promoters : Conformations and Activity of Benzolactams"" Bioorg.Med.Chem.Lett.4. 491-494 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Endo, M.Ohno, M,Hirano, A.Itai, and K.Shudo: ""Synthesis, Conformation, and Biological Activity of Teleocidin Mimics, Benzolactams. A Clarification of the Conformational Flexibility Problem in Structure-Activity Studies of Teleocidins"" J.Am.Chem.Soc.118 (in press). (1996)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Kawasaki, Y.Goda, H.Noguchi, and T.Yamada: ""Identification of Adducts Formed by Reaction of Purine Bases with a Mutagenic Anthraquinone, Lucidin : Mechanism of Mutagenicity by Anthraquinones Occurring in Rubiaceae Plants"" Chem.Pharm.Bull.42. 1971-1973 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K.Inoue, S.Kobayashi, H.Noguchi, U.Sankawa, and Y.Ebizuka: ""Spirostanol and Furostanol Glycosides of Costus speciosus (KOENIG.) SM."" Natural Medicines. 49. 336-339 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K.Ohrai, K.Kondo, M.Sodeoka, and M.Shibasaki: ""Effects of Solvents and Additives in the Asymmetric Heck Reaction of Alkenyl Triflates : Catalytic Asymmetric Synthesis of Decalin Derivatives and Determination of the Absolute Stereochemistry of (+)-Vernolepin"" J.Am.Chem.Soc.116. 11737-11748 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Sodeoka, K.Ohrai, and M.Shibasaki: ""Catalytic Asymmetric Aldol Reaction via Chiral Pd (II) Enolate in Wet DMF"" J.Org.Chem.60. 2648-2649 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Komuro, T.Higuchi, and M.Hirobe: ""Application of Chemical Cytochrome P-450 Model Systems to Studies on Drug Metabolism - VIII.Novel Metabolism of Carboxylic Acids via Oxidative Decarboxylation"" Bioorg.Med.Chem.3. 55-65 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] H.Ohtake, T.Higuchi, and M.Hirobe: ""The Highly Efficient Oxidation of Olefins, Alcohols, Sulfides and Alkanes with Heteroaromatic N-Oxides Catalyzed by Ruthenium Porphyrins"" Heterocycles. 40. 867-903 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] K.Koga and M.Shindo: ""Approaches to Catalytic Asymmetric Formation and Reactions of Lithium Enolates"" J.Synth.Org.Chem., Jpn.53. 1021-1032 (1995)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1997-03-04  

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