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1992 Fiscal Year Final Research Report Summary

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
KeywordsBakers' Yeast Reduction / Sulfur-containing Chiral Synthon / Stereoselective Reduction / Prostaglandin Intermediate / Aggregation Pheromone / Chiral Cycloalkanol / Tetrahydrothiopyran / Ranberg-Baecklund Reaction
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.

  • Research Products

    (8 results)

All Other

All Publications (8 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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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

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Published: 1994-03-24  

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