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Synthetic Studies on the Biologically Active Pyrrolizadine Derivatives Using L-Prolin as a Starting Material

Research Project

Project/Area Number 61571019
Research Category

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

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionKyoto Pharmaceutical University

Principal Investigator

IKEFA Masazumi  Kyoto Pharmaceutucal University, 薬学部, 教授 (30028857)

Co-Investigator(Kenkyū-buntansha) ISHIBASHI Hiroyuki  Kyoto Pharmaceutical University, 薬学部, 助教授 (70028869)
Project Period (FY) 1986 – 1987
Project Status Completed (Fiscal Year 1987)
Budget Amount *help
¥1,900,000 (Direct Cost: ¥1,900,000)
Fiscal Year 1987: ¥300,000 (Direct Cost: ¥300,000)
Fiscal Year 1986: ¥1,600,000 (Direct Cost: ¥1,600,000)
KeywordsL-prolinol / pyrrolizidine alkaloid / trachetanthamidine / helitridane / pseudoheliotridane / rasical cyclization / ブチロラクタム
Research Abstract

1. (-)-Tracheranthamidine was synthesized in an oprically active form by olefin by olefin cyclization of 2-(1-propenyl)pyrrolysyl-<alpha>-methylsulfinylacetamide as the key step. 2. Formal total synthesis of <plus-minus>-psudoheliotridane was achieved by radical cyclication of the N-(2-vinylpyrrolidyl)-<alpha>-chloro-<alpha>-(methylsulfinyl)acetamide as the key step. 3. Treatment of N-(2-vinylpyrrolidyl)-<alpha>-methylthioacetamide whth sodium hydride in tetrahydrofuran gave the tetrahydro-2-methylthioprrolizan-3-one.

Report

(2 results)
  • 1987 Final Research Report Summary
  • 1986 Annual Research Report
  • Research Products

    (12 results)

All Other

All Publications (12 results)

  • [Publications] 石橋弘行: J.Chem.Soc.Chem.Commun.,. 654-655 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] 石橋弘行: J.Chem.Soc.,Perkin Trans.l,. 1099-1105 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] 石橋弘行: Chem.Lett.795-798 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] 池田正澄: Heterocycles.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] 池田正澄: Heterocycles.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hiroyuki Ishibashi: "Syuthesis of optically Active (-)-Trachelanthamidine from L-Prolinol" J. Chem. Commun.,. 654-655 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hiroyuki Ishibashi: "Alkene Cyclizations of N-Alkenyl <alpha>-(methyisulphinyl)acetamides and and N-Alkenyl-<alpha>-chloro-<alpha>-(methyltio)acetamides:Novel Synthesis of Five-, Six-, and Seven-menbered Lastams" J. Chem. Sco., Parkin Trans.1. 1099-1105 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Hiroyuki Ishibashi: "Nre Entry to (gamma)-Butytolactams by Free Radical Cyclization of N-Allyl(alpha)-chloro-(alpha)-(methylthio)acetamides: Formal Total Synthesis of (+-)-Pseudoheliotridane" Chem. Lett.795-798 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Masazumi Ikeda: "Syntesis of Pyrrolizidines anf Related Compounds by Aldol Cyclization of N-<alpha>-(Methylthio)acetyl)-<alpha>-aminoaldehyde" Heterocycles. (In press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] Masazumi Ikeda: "Recent Advances in the Synthesis of Pyrrolizadines" Heterocycles.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1987 Final Research Report Summary
  • [Publications] 石橋弘行: J.Chem.Soc.,Chem.Commun.654-655 (1986)

    • Related Report
      1986 Annual Research Report
  • [Publications] 石橋弘行: Chem.Lett.(1987)

    • Related Report
      1986 Annual Research Report

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

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