• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Efficient Synthesis of Sulfur-functionalized Cycloalkanol as a Chiral Synthon.

Research Project

Project/Area Number 03453027
Research Category

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

Allocation TypeSingle-year Grants
Research Field 有機化学一般
Research InstitutionMie University

Principal Investigator

FUJISAWA Tamotsu  Mie University,(Department of Chemistry for Materials)Faculty of Engineering, 工学部, 教授 (60115730)

Project Period (FY) 1991 – 1992
Project Status Completed (Fiscal Year 1992)
Budget Amount *help
¥8,300,000 (Direct Cost: ¥8,300,000)
Fiscal Year 1992: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 1991: ¥7,200,000 (Direct Cost: ¥7,200,000)
KeywordsBakers' Yeast Reduction / Sulfur-containing Chiral Synthon / Stereoselective Reduction / Prostaglandin Intermediate / Aggregation Pheromone / Chiral Cycloalkanol / Tetrahydrothiopyran / Ranberg-Baecklund Reaction / 光学活性β-ケトール / サイトフイルアー / 光学活性シクロアロカノ-ル / RambergーBaecklund反応
Research Abstract

The stereoselective reduction of sulfur-functionalized cyclic ketones with bakers' yeast leading to cyclic carbinols bearing two adjacent chiral centers and the subsequent transformations into biologically interesting compounds were studied. The bakers' yeast reduction of 2-phenylthiocyclopentanone, 2-phenylthiocyclohexanone, and 2-phenylthio-2-cyclopentenones proceeds well to give optically pure (1S,2R)-1-phenylthio-cycloalkanols. Furthermore, 4-oxo-3-tetrahydrothiopyranylacetates were reduced with bakers' yeast to give optically pure (3S,4S)-4-hydroxy-3-tetrahydrothiopyranylacetate, which was converted into an optically pure prostaglandin intermediate. The bakers' yeast reduction of 3-acyltetrahydrothiopyran-4-ones gave (3S,4S)-3-acyl-4-hydroxytetrahydro-thiopyrane with high regio-and enantioselectivity. In particular, the reduction of 3-propionyltetrahydrothiopyran-4- one took place regioselectively to give a single (3R,4S)-isomer in optically pure form in good yield, and the subsequent desulfurization by Raney-Ni gave the insect aggregation pheromone, (-)-(4R,5S)-Sitophilure with high optical purity.

Report

(3 results)
  • 1992 Annual Research Report   Final Research Report Summary
  • 1991 Annual Research Report
  • Research Products

    (14 results)

All Other

All Publications (14 results)

  • [Publications] T.Fujusawa: "A Short Synthesis of (_-)_-(4R,5S)_- Sitophilure using the Regio- and stereoselective Reduction of 3_-Acyltetrahydrothipyran_-4_-ones with Bakers'Yeast" Tetrahedron Lett.33. 5567-5570 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T.Fujusawa: "Enantioseloctive Reduction of 4_-Oxo_-3_-tetrahydro-thiopyranylacetate with Bakers'Yeast" Tetrahedron Lett.32. 7055-7058 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T.Fujusawa: "Highly Enantio- and Diastereo-selective Reduction of Sulfur-functionalized Cyclic Ketones with Bakers'Yeast" Tetrahedron Lett.32. 399-400 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T.Fujusawa: "Stereocontrol in Bakers'Yeast Reduction Leading to Natural Product Syntheses" Kagaku Zokann. 119. 49-60 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T.Fujisawa,B.I.Mobele,M.Shimizu: "A Short Synthesis of(-)-(4R,5S)-Sitophilure using the Regio-and Stereoselective Reduction of 3-Acyl-tetrahydrothiopyran-4-ones with Bakers' Yeast" Tetrahedrom Lett.33. 5567-5570 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T.Fujisawa,B.I.Mobele,M.Shimizu: "Enantioselective Reduction of 4-Oxo-3-tetrahydrothiopyranylacetate with Bakers' Yeast" Tetrahedrom Lett.32. 7055-7058 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T.Fujisawa,K.Yamanaka,B.I.Mobele,M.Shimizu: "Highly Enantio-and Diastereo-selective Reduction of Sulfur-functionalized Cyclic Ketones with Bakers' Yeast" Tetrahedron Lett.32. 399-400 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T.Fujisawa, Stereocontrol in Bakers' Yeast: "Reduction Leading to Natural Product Syntheses" Kagaku Zokann. 119. 49-60 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T.Fujisawa: "A Short Synthesis of(-)-(4R,5S)-Sitophilure using the Regio-and Stereoselective Reduction of 3-Acyltetrahydrothiopyran-4-ones with Bakers'Yeast" Tetrahedron Lett.33. 5567-5570 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] T.Fujisawa: "Enantioselective Reduction of 4-Oxo-3-tetrahydrothiopyranylacetate with Bakers'Yeast," Tetrahedron Lett.32. 7055-7058 (1991)

    • Related Report
      1992 Annual Research Report
  • [Publications] 藤澤 有: "パン酵母還元における選択性の制御とその応用" 化学増刊119 ハイブリッドプロセスによる有用物質生産. 49-60 (1991)

    • Related Report
      1992 Annual Research Report
  • [Publications] T.Fujisawa: "Highly Enantio-and Diastereoselective Reduction of Sulfur-functionalized Cyclic Ketones with Bakers'Yeast" Tetrahedron Lett.32. 399-400 (1991)

    • Related Report
      1992 Annual Research Report
  • [Publications] T.Fujisawa: "Higly Enantioーand Diastereoselective reduction of SulfurーFunctionalized Cyclic Ketones with Bader's Yeast" Tetrahedoron Letters. 32. 399-400 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] T.Fujisawa: "Enantioselective Reduction of 4ーOxoー3ーtetrahydrothiopyranylacetates with Bakers'Yeast and Application to the Synthesis of a Prostaglandin Intermediate in Optically Pure form." Tetrahedoron Letters. 32. 7055-7058 (1991)

    • Related Report
      1991 Annual Research Report

URL: 

Published: 1991-04-01   Modified: 2016-04-21  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi