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Study on the environmentally-suitable synthesis of plant conservation materials and medicines

Research Project

Project/Area Number 07555282
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section試験
Research Field 有機工業化学
Research InstitutionOkayama University

Principal Investigator

TSUBOI Sadao  Okayama University, Faculty of Environmental Science and Technology, Professor, 環境理工学部, 教授 (00032954)

Co-Investigator(Kenkyū-buntansha) NAKASHIMA Shuhei  Faculty of Agriculture, Okayama University Associate Professor, 農学部, 助教授 (10100950)
小林 主一  北興化学工業株式会社, 開発研究所, 研究員
宇高 正徳  岡山大学, 工学部, 教授 (30033153)
Project Period (FY) 1995 – 1996
Project Status Completed (Fiscal Year 1996)
Budget Amount *help
¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 1996: ¥1,000,000 (Direct Cost: ¥1,000,000)
Keywordsplant conservation material / bakers' yeast / lipase / optically active compound / biological catalyst / medicine / antitumor compound / highly selective reaction / 昆虫フェロモン / (-)-ディスパーラー / ペスタロチン / 高立体選択的合成
Research Abstract

In this project, we suceeded in the syntheses of chiral alcohols, epoxides, and gamma-butenolides with high optical purities from readily-available starting materials by using environmentally-suitable materials such as bakers' yeast and hydrolysis enzyme, lipase.. Furthermore, plant conservation materials such as insect pheromones and plant hormones, medicines, and their key-intermediates were synthesized from products described above, and biological activities of their synthesized materials are under investigaiton. Major results are summarized as follows :
1. Optically active malic acid, which is a useful key-intermediate in the synthesis of natural products, was synthesized.
2. Optically active 3-chloro-2-hydroxyalkanoates were synthesized, and the total synthesis of (-) -disparlure was established.
3. Both enantiomers of gamma-butenolides were synthesized with high selectivity, and these were applied for the syntheses of (3aS,6aS) -ethysolide, whisky lactone, and (-) -avenaciolide.
4. Optically active alpha-hydroxyaldehydes and glycidic esters, which are useful key-intermediates for the synthesis of pestalotin, accelating the growth of plants, were synthesized.
5. Flourine analog of methyl (Z) -5-tetradecenoate, a sex pheromone of soybean beetle was synthesized.

Report

(3 results)
  • 1996 Annual Research Report   Final Research Report Summary
  • 1995 Annual Research Report
  • Research Products

    (5 results)

All Other

All Publications (5 results)

  • [Publications] 坪井貞夫: "Asymmetric Synthesis of Optically Active Malic Afid" J.Fac.Environ.Sci.and Tech.,Okayama Univ.1. 205-210 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 坪井貞夫: "Lipase-catalyzed kinetic resolution of 3-chloro-2-hydroxyalkanoates.Its application for the synthesis of (-) -disparlure" Tetrahedron : Asymmetry. 8. 375-379 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Sadao Tsuboi, Shin-ichiro Ono, and Masanori Utaka: "Aymmetric Synthesis of Optically Active Malic Acid" J.Fac.Environ.Sci.and Tech., Okayama Univ.Vol.1 (No.1). 205-210 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Sadao Tsuboi, Nobuyuki Yamafuji, and Masanori Utaka: "Lipase-catalyzed kinetic resolution of 3-chloro-2-hydroxyalkanoates. Its application for the synthesis of (-) -disparlure" Tetrahedron : Asymmetry. Vo.8 (No.3). 375-379 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 坪井貞夫: "C : Pase-Catalyzed kinetic resolution of 3-chlors-2-hydroxy-alkanoates. Its application for the synthesis of (-)-disparlure" Tetrahedron Aeymmetry. 8(印刷中). (1997)

    • Related Report
      1996 Annual Research Report

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Published: 1996-04-01   Modified: 2016-04-21  

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