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Asymmetric Synthesis of Heterocyclic Compounds

Research Project

Project/Area Number 60571009
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionKobe Women's College of Pharmacy

Principal Investigator

NAITO Takeaki  Assistant Professor, Kobe Women's College of Pharmacy, 薬学部, 助教授 (00068339)

Co-Investigator(Kenkyū-buntansha) MIYATA Okiko  Lecturer, Kobe Women's College of Pharmacy, 薬学部, 助手 (90102110)
KIGUCHI Toshiko  Lecturer, Kobe Women's College of Pharmacy, 薬学部, 講師 (70068344)
Project Period (FY) 1985 – 1986
Project Status Completed (Fiscal Year 1986)
Budget Amount *help
¥1,400,000 (Direct Cost: ¥1,400,000)
Fiscal Year 1986: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1985: ¥1,000,000 (Direct Cost: ¥1,000,000)
KeywordsAsymmetric Synthesis / Heterocyclic Compounds / Enamides / Isoquinoline / Indole / Photocyclization / Alkaloids / エメチン
Research Abstract

A new and simple synthetic methodology for the optically active heterocyclic compounds was developed by the application of two types of chiral circumstances to the photocyclizations of the anilides and enamides which are known to proceed via a common intermediate having two functional groups, the enolate and iminium moieties.
1. Asymmetric synthesis of quinolones by photocyclization of anilides involving enantioselective protonation of enolate moiety When we used a chiral dibasic acid possessing a <C_2> axis such as di-p-toluoyltartaric acid during the course of irradiation of anilides, optically active quinolones were obtained as a result of enantioselective protonation to the intermediate in moderate chemical and optical yields.
2. Asymmetric synthesis of isoquinolines and related compounds by photocyclization of enamides involving enantioselective reduction of iminium moiety Irradiation of enamides in the presence of chiral metal hydride complex of lithium aluminum hydride-chiral amino-alcohol afforded the optically active 8-oxoberbines, thus completing the asymmetric synthesis of (-)-Xylopinine.

Report

(1 results)
  • 1986 Final Research Report Summary
  • Research Products

    (12 results)

All Other

All Publications (12 results)

  • [Publications] 内藤猛章: Heterocycles. 16. 1141-1143 (1981)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] 内藤猛章: Heterocycles. 20. 779-782 (1983)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] 内藤猛章: Heterocycles. 22. 237-240 (1984)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] 内藤猛章: J.Chem.Soc.,Chem.Commun.,. 1611-1612 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] 内藤猛章: J.Chem.Soc.,Perkin Trans.l,. 487-491 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] 内藤猛章: 薬学研究の進歩、研究成果報告書1(薬学研究奨励財団). 1. 88-104 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Takeaki Naito: "Reductive Photocyclization of Enamide in the Presence of a Chiral Metal Hydride Complex-Asymmetric Synthesis of Xylopinine" Heterocycles. 16. 1141-1143 (1981)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Takeaki Naito: "Asymmetric Synthesis of Dibenzo[a,g]quinolizines Related to Protoberberine Alkaloids" Heterocycles. 20. 779-782 (1983)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Takeaki Naito: "Asymmetric Photocyclization of N- <alpha> , <beta> -Unsaturated Acylanilides" Heterocycles. 22. 237-240 (1984)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Takeaki Naito: "A General Strategy for the Synthesis of Ipecac and Heteroyohimbine Alkaloids" J. Chem. Soc., Chem. Commun.,. 1611-1612 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Takeaki Naito: "Photocyclisation of Enamides. Part 23. Reductive Photocyclisation of Enamides" J. Chem. Soc., Perkin Trans. 1,. 487-491 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Takeaki Naito: The Research Foundation for Pharmaceutical Sciences. Reductive Photocyclization of Enamides and Asymmetric Synthesis of Alkaloids, 88-104 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary

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Published: 1987-03-31   Modified: 2016-04-21  

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