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Synthesis of Cyclopentane-Macrolides Based on Lewis Acid Mediated Cyclization of Chiral Epoxy-Alcohols

Research Project

Project/Area Number 01571137
Research Category

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

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionTohoku University

Principal Investigator

YATAKEYAMA Susumi  Tohoku University Pharmaceutical Institute Research ASsociate, 薬学部, 助手 (20143000)

Project Period (FY) 1989 – 1991
Project Status Completed (Fiscal Year 1991)
Budget Amount *help
¥1,900,000 (Direct Cost: ¥1,900,000)
Fiscal Year 1991: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1990: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 1989: ¥900,000 (Direct Cost: ¥900,000)
KeywordsSharpless asymmetric epoxidation / Lewis acid mediated cyclization / Substituted cyclopentane / Enantiocontrolled synthesis / Brefeldin A / Brefeldin C / Macrolide antibiotic / Chiral epoxy-alcohol / アリルシラン / 抗生物質 / マクロリド / キラル置換シクロペンタン / Hybridialactone / Ecklonialactone A / (R,R)ー3,4ージヒドロキシメチルシクロペンテン / ルイス酸触媒下の環化 / ブレフェルディンA / キラル合成 / キラルシクロペンタン / ブレフェルディンC
Research Abstract

In the course of investigation concerning intramolecular Lewis acid mediated nucleophilic opening of epoxy-alcohols, we have developed an enantioselective route to a substituted cyclopentane 2 from an allyl alcohol 1 through four manipulations ; i)Sharpless asymmetric epoxidation, ii)Lewis acid mediated cyclization ; iii)protection as acetonide ; iv)ozonolysis followed by base-catalyzed epimerization. The generality of this method was proved by the fact that regardless of the stereo- and regio-chemistry of pre-exsisting substituents(R^1 and/or R^2)of 1, tri- or four-substituted cyclopentanes 2 with 1, 2-trans configuration were obtained in high enantiomeric excess(>90% ee). The synthetic utility of this method was demonstrated by the achievement of enantiocontrolled syntheses of(+)-brefeldin A(3)and(+)-brefeldin C(4)from 2(R^1=H, R^2=OBn or R^1=R^2=H).
brefeldin C(4)from 2(R'=H, R2=OBn or RI=R2=H).

Report

(4 results)
  • 1991 Annual Research Report   Final Research Report Summary
  • 1990 Annual Research Report
  • 1989 Annual Research Report
  • Research Products

    (6 results)

All Other

All Publications (6 results)

  • [Publications] Susumi Hatakeyama: "Total Synthesis of (+)-Brefeldin C via Lewis Acid Mediated Cyclization of an Epoxy-Allylsilane" Tetrahedron Letters. 30. 4845-4848 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Susumi Hatakeyama: "Enantioselective Preparation of Functionalized Cyclopentanes Using Lewis Acid Mediated Cyclization of Epoxy Allylsilanes:Enantiocontrolled Total Synthesis of (+)-Brefeldin A" Synlett. 691-693 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Susumi Hatakeyama: "Total Synthesis of (+)-Brefeldin C via Lewis Acid Mediated Cyclization of An Epoxy-Allylsilane" Tetrahedron Lett.30. 4845-4848 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Susumi Hatakeyama: "Enantioselective Preparation of Functionalized Cyclopentanes Using Lewis Acid Mediated Cyclization of Epoxy Allylsilanes : Enantiocontrolled Total Synthesis of (+)-Brefeldin A" Synlett. 691-693 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Susumi Hatakeyama: "Enantioselective Preparation of Functionalized Cyclopentanes Using Lewis Acid Mediated Cyclization of Epoxy Allylsilanes:Enanticontrolled Total Synthesis of (+)ーBrefeldin A" Synlett. 691-693 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] Susumi Hatakeyama: "Total Synthesis of (+)-Brefeldin C Via Lewis Acid Mediated Cyclization of an Epoxy-Allylsilane" Tetrahedron Letters. 30. 4845-4848 (1989)

    • Related Report
      1989 Annual Research Report

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Published: 1989-04-01   Modified: 2016-04-21  

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