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1991 Fiscal Year Final Research Report Summary

Development of a General Method for Synthesis of Optically Active Tertiarv Allylic Alcohols and Its Applications

Research Project

Project/Area Number 02453091
Research Category

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

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionTokyo Institute of Technology

Principal Investigator

SATO Fumie  Tokyo Institute of Technology, Biomolecular Engineering, Professor, 生命理工学部, 教授 (50016606)

Co-Investigator(Kenkyū-buntansha) OKAMOTO Sentaro  Tokyo Institute of Technology Biomolecular Engineering, Research Associate, 生命理工学部, 助手 (00201989)
KOBAYASHI Yuichi  Tokyo Institute of Technology Biomolecular Engineering, Associate Professor, 生命理工学部, 助教授 (90153650)
Project Period (FY) 1990 – 1991
KeywordsChiral / Asymmetric Synthesis / Allylic Alcohols / Tertiary Alcohols / Prostaglandin / Arbaprostil / Epoxy Alcohol
Research Abstract

Tertiary allylic alcohols are incorporated in the structures of a variety of natural products and commercially important pharmaceuticals. Equally significant is the latent faculties of tertiary allylic alcohols as versatile synthetic intermediates. Only a few methods, however, are available for preparation of them in a chiral form and these methods so far developed suffer from some disadvantages such as low optical purity and/or lack of generality. We have now succeeded in developing practical and general synthetic method of tertiary allylic alcohols.
Thus, the reaction of beta-trimethylsilyl-alpha, beta-epoxyketones, readily prepared in a chiral form by using the Sharpless kinetic resolution of gamma-trimethytsilyl secondary allylic alcohols as a key reaction, with Grignard reagents proceeds highly diastereoselectively to afford optically active gamma-trimethylsilyl-beta, gamma-epoxy tertiary alcohols. gamma-Trimethylsilyl-beta, gamma-epoxy tertiary alcohols reacts with nucleophils affords the corresponding tertiary allylic alcohols via regionspecific ring opening followed by the Peterson olefination reaction. The application of the tertiary allylic alcohols thus obtained to the synthesis of prostaglandin derivative, Arbaprostil was carried out.

  • Research Products

    (10 results)

All Other

All Publications (10 results)

  • [Publications] Takayori Ito: "Practical Method for Synthesis of Optically Pure Propargylic Alcohols" Tetrahedron Letters. 30. 7083-7086 (1989)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takayori Ito: "Synthesis of Optically Active α-Trimethylsilyl △^<α,β>-Butenolides and Their Conversion into Various Butenolides and Saturated γ-Lactones" Tetrahedron Letters. 31. 6399-6402 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yuichi Kobayashi: "Highly Stereocontrolled Total Synthesis of Leukotriene B_4,20-Hydroxyleukotriene B_4,Leukotriene B_3,and Their Analogues" J.Org.Chem.55. 5324-5335 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Sentaro Okamoto: "Synthesis of Optically Active γ-Trimethylsilyl-β,γ-epoxy Tertiary Alcohols by the Diastereoselective Addition Reaction of Trimethylsilyl-α,β-epoxyketones with Grignard Reagent" Tetrahedron Letters. 32. 5789-5792 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Sentaro Okamoto: "Highly Efficient and General Method for Synthesis of Tertiary Allylic Alcohols in a Chiral Form.Synthesis of Arbaprostil" Tetrahedron Letters. 32. 5793-5796 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takayori Ito: "Practical Method for Synthesis of Optically Pure Propargylic Alcohols" Tetrahedron Lett.30. 7083-7086 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Takayori Ito: "Synthesis of Optically Active beta-Trimethylsilyl DELTA^<alpha, beta>-Butenolides and Their Conversion into Various Butenolides and Saturated gamma-Lactones" Tetrahedron Lett.31. 6399-6402 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yuichi Kobayashi: "Highly Stereocontrolled Total Synthesis of Leukotriene B_4, 20-HydroxyLeukotriene B_4, Leukotriene B_3, and Their Analogues" J. Org. Chem.55. 5324-5335 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Sentaro Okamoto: "Synthesis of Optically Active gamma-Trimethylsilyl-beta, gamma-epoxy Tertiary Alcohols by the Diastereoselecive Addition Reaction of beta-Trimethyl-silyl-alpha, beta-epoxyketones with Grignard Reagent" Tetrahedron Lett.32. 5789-5792 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Sentaro Okamoto: "Highly Efficient and General Method for Synthesis of Tertiary Allylic Alcohols in a Chiral Form. Synthesis of Arbaprostil" Tetrahedron Lett.32. 5793-5796 (1991)

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

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Published: 1993-03-16  

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