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

植物保护材料和药物的环保合成研究

基本信息

批准号：
07555282
负责人：
TSUBOI Sadao
金额：
$ 0.64万
依托单位：
Okayama University
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (A)
财政年份：
1995
资助国家：
日本
起止时间：
1995 至 1996
项目状态：
已结题

来源：
https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-07555282/
关键词：
plant 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

项目摘要

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.

本项目利用面包酵母、水解酶、脂肪酶等环境友好型原料，从容易获得的原料出发，成功地合成了高光学纯度的手性醇、环氧化物、γ-丁烯内酯。此外，还合成了昆虫信息素、植物激素等植物保护材料、药物及其关键中间体，并对其生物活性进行了研究。主要研究结果如下：1.合成了光学活性的苹果酸，它是合成天然产物的重要中间体.合成了光学活性的3-氯-2-羟基烷酸酯类化合物，建立了（-）-赤藓糖醇的全合成方法.高选择性地合成了γ-丁烯内酯的两种对映体，并将其应用于（3aS，6aS）-乙内酯、威士忌内酯和（-）-燕麦内酯的合成.合成了具有光学活性的α-羟基醛和缩水甘油酸酯，它们是合成pestalotin的重要中间体，具有促进植物生长的作用.合成了大豆甲虫性信息素（Z）-5-十四烯酸甲酯的氟类似物。