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

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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.