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

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
Project Status Completed (Fiscal Year 1992)
Budget Amount *help
¥6,800,000 (Direct Cost: ¥6,800,000)
Fiscal Year 1992: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1991: ¥1,800,000 (Direct Cost: ¥1,800,000)
Fiscal Year 1990: ¥4,500,000 (Direct Cost: ¥4,500,000)
Keywordsenantiocontrolled synthesis / chiral acetylene alcohol / chiral building block / natural product synthesis / lipase / Katsuki-Sharpless reaction / enantiocomplementary resolution / enantioconvergent resolution / キラル3‐ヒドロキシアセチレン / キラル4‐ヒドロキシアセチレン / アシル化不斉分割 / 脱アシル化不斉分割 / エナンチオ相補分割 / エナンチオ集約分割 / 光延反応 / キラルαーヒドロキシアセチレン / キラルβーヒドロキシアセチレン / フィト-ル / ビタミンE / ワライタケ成分 / ニコラス反応 / コンパクチンラクトン / マイシノリド / キラルー3ーヒドロキシアセチレン / キラル4ーヒドロキシアセチレン / 香月、ーシャ-プレス反応 / キラルοーベンジルグリシド-ル / メバロン酸ラクトン / コンパクチン
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.

Report

(4 results)
  • 1992 Annual Research Report   Final Research Report Summary
  • 1991 Annual Research Report
  • 1990 Annual Research Report
  • Research Products

    (25 results)

All Other

All Publications (25 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
    • Related Report
      1992 Final Research Report Summary
  • [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
    • Related Report
      1992 Final Research Report Summary
  • [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
    • Related Report
      1992 Final Research Report Summary
  • [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
    • Related Report
      1992 Final Research Report Summary
  • [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
    • Related Report
      1992 Final Research Report Summary
  • [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
    • Related Report
      1992 Final Research Report Summary
  • [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
    • Related Report
      1992 Final Research Report Summary
  • [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
    • Related Report
      1992 Final Research Report Summary
  • [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
    • Related Report
      1992 Final Research Report Summary
  • [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
    • Related Report
      1992 Final Research Report Summary
  • [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
    • Related Report
      1992 Final Research Report Summary
  • [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
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Seiichi Takano: "A New Enantiospecific Route to (-)‐Kainic Acid via the Intramolecular Pauson-Khand Reaction" J.Chem.Soc.,Chem.Commun.169-170 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Seiichi Takano: "An Enantiospecific Route to (6R)‐(-)‐Massoialactone and (4R,6R)‐(+)‐4‐Hydroxy‐6‐pentylvalerolactone" Tetrahedron:Asymmetry. 3. 533-534 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Seiichi Takano: "Stereocontrolled Route to the δ‐Benzylidenemethy1‐β‐hydroxy‐δ‐lactone System Utilizing a New Chiral Epoxyacetylene Building Block" Tetrahedron:Asymmetry. 3. 853-856 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Seiichi Takano: "Enantiocomplementary Resolution of 4‐Hydroxy‐5‐(4‐methoxyphenoxy)‐1‐Pentyne Using the Same Lipase" Tetrahedron:Asymmetry. 4. 157-160 (1993)

    • Related Report
      1992 Annual Research Report
  • [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)

    • Related Report
      1992 Annual Research Report
  • [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 and Vincamine" Tetrahedron:Asymmetry.

    • Related Report
      1992 Annual Research Report
  • [Publications] Seiichi Takano: "The First Enantiocontrolled Synthesis of(3S,8S)ー(ー)ー4,6ーDecadiyneー1,3,8ーtriol from a Toxic Mushroom Gymnopilus Spectabilis" Tetrahedron Letters. 32. 2797-2798 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Seiichi Takano: "The Enantioselective Total Synthesis of Natural (ー)ーAphanorphine" J.Chem.Soc.,Chem.Commun.290-292 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] Seiichi Takano: "Enantiocontrolled Synthesis of Natural (+)ーBakuchiol" Tetrahedron Letters. 31. 3325-3326 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] Seiichi Takano: "A convergent Enantiocontrolled Route to Mevalonolactone and Vitamin E from (__S)ー__OーBenzylglycidol" Tetrahedron Letters. 31. 3619-3622 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] Seiichi Takano: "Efficient Preparation of Potentially Useful Chiral Cyclopentanoid Building Blocks Based on C_2 Symmetry" Synlett. 453-454 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] Seiichi Takano: "Concise Enantioー and Stereoーcontrolled Synthesis of (+)ーEquilenin Using Chiral Cyclopentadienone Synthon" J.Chem.Soc.,Chem.Commun.1544-1546 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] Seiichi Takano: "An Efficient Stereoselective Preparation of Vitamin E (αーTocopherol) from Phytol" Synlett. 451-452 (1990)

    • Related Report
      1990 Annual Research Report

URL: 

Published: 1990-04-01   Modified: 2016-04-21  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi