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1992 Fiscal Year Final Research Report Summary

Preparation and Utilization of Chiral alpha-and beta-Hydroxyacetylenes

Research Project

Project/Area Number 02453139
Research Category

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

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionTOHOKU UNIVERSITY

Principal Investigator

OGASAWARA Kunio  Tohoku University Pharmaceutical Institute Associate Professor, 薬学部, 助教授 (60004602)

Project Period (FY) 1990 – 1992
Keywordsenantiocontrolled synthesis / chiral acetylene alcohol / chiral building block / natural product synthesis / lipase / Katsuki-Sharpless reaction / enantiocomplementary resolution / enantioconvergent resolution
Research Abstract

Some chiral acetylene building blocks having hydroxy functionality on alpha- or beta-stereogenic center have been prepared in efficient manners involving enzymatic reaction using lipase and asymmetric reaction employing the Katsuki-Sharpless asymmetric epoxidation reaction.
Versatile utility of these acetylene derivatives as chiral building blocks has been demonstrated by transforming these into a wide variety of natural product ranging from simple monoterpenoids to complex natural products, such as alkaloids, aminoacids, and poly ketides in enantiocontrolled ways as well as by devising specific reactions making use of these chiral acetylene compounds.

  • Research Products

    (12 results)

All Other

All Publications (12 results)

  • [Publications] Seiichi Takano: "A New Enantiospecific Route to(-)-Kainic Acid via the Intramolecular Pauson-Khand Reaction" J.Chem.Soc.,Chem.Commun.169-170 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Seiichi Takano: "An Enantiospecific Route to(6R)-(-)-Massoialactone and (4R,6R)-(+)-4-Hydroxy-6-pentylvalerolactone" Tetrahedron:Asymmetry. 3. 533-534 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Seiichi Takano: "Stereocontrolled Route to the δ-Benzylidenemethy-β-hydroxy-δ-lactone System Utilizing a New Chiral Epoxyacetylene Building Block" Tetrahedron:Asymmetry. 3. 853-856 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Seiichi Takano: "Enantiocomplementary Resolution of 4-Hydroxy-5-(4-methoxyphenoxy)-1-pentyne Usin the Same Lipase" Tetrahedron:Asymmetry. 4. 157-160 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Seiichi Takano: "Enantioconvergent Synthesis of a Promising HMG Co-A Reductase Inhibitor NK-104 from Both Enantiomers of Epichlorohydrin" Tetrahedron:Asymmetry. 4. 201-204 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Seiichi Takano: "Enantiocomplementary Preparation of Optically Pure 2-Trimethylsilylethyny1-2-cyclopentenol by Homochiralization of Racemic Precursors:A New Route to the key Intermediate of 1,25-Dihydrocholecalciferol" Tetrahedron:Asymmetry.

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Seiichi Takano: "A New Enantiospecific Route to (-)-Kainic Acid via the Intramolecular Pauson-Khand Reaction" J.Chem. Soc., Chem. Commun.169-170 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Seiichi Takano: "An Enantiospecific Route to (6R)-(-)-Massoialactone and (4R,6R)-(+)-4-Hydroxy-6-pentylvalerolactone" Tetrahedron: Asymmetry. 3. 533-534 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Seiichi Takano: "Stereocontrolled Route to the delta-Benzylidenemethyl-beta-hydroxy-delta-lactone System Utilizing a New Chiral Epoxyacetylene Building Block" Tetrahedron: Asymmetry. 3. 853-856 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Seiichi Takano: "Enantiocomplementary Resolution of 4-Hydroxy-5-(4-methoxy-phenoxy)-1-pentyne Using the Same Lipase" Tetrahedron: Asymmetry. 4. 157-160 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Seiichi Takano: "Enantioconvergent Synthesis of a Promising HMG Co-A Reductase Inhibitor NK-104 from Both Enantiomers of Epichlorohydrin" Tetrahedron: Asymmetry. 4. 201-204 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Seiichi Takano: "Enantiocomplementary Preparation of Optically Pure 2-Trimethyl- silylethynyl-2-cyclopentenol by Homochiralization of Racemic Precursors: A New Route to the Key Intermediate of 1,25- Dihydrocholecalciferol and Vincamine" Tetrahedron: Asymmetry.

    • 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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