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Origination of functional chiral building blocks using asymmetric acylation and application to the synthesis of biologically active compounds

Research Project

Project/Area Number 05671743
Research Category

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

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionTOYAMA MEDICAL AND PHARMACEUTICAL UNIVERSITY

Principal Investigator

TAKAHATA Hiroki  Toyama Medical & Pharmaceutical University, Faculty of Pharmaceutical Sciences, Associate Professor, 薬学部, 助教授 (00109109)

Co-Investigator(Kenkyū-buntansha) MOMOSE Takefumi  Toyama Medical & Pharmaceutical University, Faculty of Pharmaceutical Sciences,, 薬学部, 教授 (50028833)
Project Period (FY) 1993 – 1994
Project Status Completed (Fiscal Year 1994)
Budget Amount *help
¥1,900,000 (Direct Cost: ¥1,900,000)
Fiscal Year 1994: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 1993: ¥1,100,000 (Direct Cost: ¥1,100,000)
KeywordsAsymmetric acylation / Lipase / Chiral building block / Chiral synthesis / gamma-Butyrolactone / Intramolecular lactonization / Stereoselective synthesis / Insect pheromone / ヨードラクトン化 / オキシラクトン化
Research Abstract

Enzymes are now recognized as substrate-specific and highly enantioselective catalyst for asymmetric synthesis. In particular, lipases have recently been used for biocatalytic resolutions on the basis of the admission of organic solvents as reaction media.We succeeded immobilized lipase-mediated resolution of N,N-dialky1-3-hydroxy-4-pentenamides, unsuccessful in resolution by the Katsuki-Sharpless asymmetric epoxidation. Iodolactonizaion of thus prepared homochiral amides and oxy-lactonization of O-protected homochiral amides proceeded stereoselectively, affording both enantiomers of cis-3,4-disubstituted gamma-lactone and both enantiomers of trans-3,4, disubstituted gamma-lactone preferentially, respectively.These gamma-lactones have been used as chiral building blocks for the synthesis of biological active compounds such as litsenolides, (+) -blastimycinone, NFX-2, NFX-4, metabolites from Gorgonian Plexaura flava, and muscarine.Especially, cis-3,4-disubstituted gamma-lactones were served as the masked butenolide chirons and a concise synthesis of (+) -trans-wisky and (+) -trans-cognac lactones, (-) -methylenolactocin, (+) -nephrosteranic acid, and (+) -roccellaric acid has been achieved.In addition, these gamma-lactones have been apllied as chiral carbon five building blocks for the synthesis of insect pheromons.

Report

(3 results)
  • 1994 Annual Research Report   Final Research Report Summary
  • 1993 Annual Research Report
  • Research Products

    (15 results)

All Other

All Publications (15 results)

  • [Publications] 高畑広紀: "Enzymatic lesolution of N_1N-dialkyl-3-hydroxy-4-pentenamide,unsnccessful in resolution by the Katsuki-Sharpless asymmetric epoxidation" Tetrahedron:Asymmetry. 4. 1041-1042 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] 高畑広紀: "高選択的なヘテロ環化反応の開発と生物活性物質の合成への応用" 薬学雑誌. 113. 737-759 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] 高畑広紀: "New entry to Chirul butenolide synthons.Application to expeditious syntheses of (+) nephrosterunic acid,(+)-trans-whisky lactone,and (+)-trans-cognac lactone" Tetrahedron Letters. 35. 4123-4124 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] 高畑広紀: "New synthesis of all four isomers of 3-hydroxy-4-methy-γ-buthrolactone by stereoselective intramolecular lactonization to asymmetric synthesis of biologically active compomds"

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Journal of Organic Chemistry. 59. 7201-7208 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Takahata, Hiroki: "Enzymic resolution of N,N-dialky1-3-hydroxy-4-pentenamides, unsuccessful in resolution by the Katsuki-Sharpless asymmetric epoxidation" Tetrahedron : Asymmetry. 4. 1041-1042 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Takahata, Hiroki: "Highly selective intramoleccular heterocyclization and its application to synthesis of biologically active compounds" Yakugaku Zasshi. 113. 737-759 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Takahata, Hiroki: "New entry to chiral butenolide synthons.Application to expeditious syntheses of (+) -nephrosteranic acid, (+) -trans-whisky lactone, and (+) -trans-cognac lactone" Tetrahedron Letters. 35. 4123-4124 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Takahata, Hiroki: "New Synthesis of All Four Isomers of 3-Hydroxy-4-methyl-gamma-butyrolactone by Stereoselective Intramolecular Lactonization. Application to Asymmetric Synthesis of Biologically Active Compounds" Journal of Organic Chemistry. 59. 7201-7208 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] 高畑広紀: "Enzymatic resolution of N,N-dialkye-3-hydroxy-4-pentanamicles,unsucceassful in resolntion by the Ketsuki-Sharpless asymmetric epoxidation" Tetrahedron Asymmetry. 4. 1041-1042 (1993)

    • Related Report
      1994 Annual Research Report
  • [Publications] 高畑広紀: "高選択的なヘテロ環化反応の開発と生物活性物質の合成への応用" 薬学雑誌. 113. 737-759 (1993)

    • Related Report
      1994 Annual Research Report
  • [Publications] 高畑広紀: "New entry to chiral butenolide synthons.Application to expeditions sgntheses of (+)-nephrosteranic acid,(+)-trans-whisky lactone,and (+)-trans-cognac lactone" Tetrahedron Letlers. 35. 4123-4124 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] 高畑広紀: "New Synthesis of all four isomers of 3-hydroxy-4-methyl-γ-butyro lactone by stereoselective intramokuln lactonization to usymmetric synthesis of biologically active compounds" Journal of Organic Chemistry. 59. 7201-7208 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Takahata 他3名: "Enzymatic Resolution of N,N-Dialkyl-3-hydroxy-4-Pentenamides,Unsmashd in Resolution by the Katsuki-Sharpless Asymmetric Epoxidation" Terahedron!Asymmetry. 4. 1041-1042 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] 高畑広紀: "高選的なヘテロ環化反応の開発と生物活性物質の合成への応用" 薬学雑誌. 113. 737-759 (1993)

    • Related Report
      1993 Annual Research Report

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Published: 1993-04-01   Modified: 2016-04-21  

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