Study on Asymmetric Synthesis and Application to physiological Active Compound

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1. Asymmetric Synthesis of Some Carbonyl Compounds Using 1-Chloroalkyl p-Tolyl Sulfoxides. Practical synthetic procedure of optical active 1-chloroalkyl p-tolyl sulfoxides was investigated, and asymmetric synthesis of optical active epoxides, allylic alcohols, amino-aldehydes, and aziridines had been sucseccful.(1) Asymmetric synthesis of alpha-hydroxy-carboxylic acids, esters, amides, acetylenes, propargylic alcohols starting from the optical active 1-chloroalkyl p-tolyl sulfoxides were successful.(2) Synthesis of optical active amido compounds by the asymmetric Favorskii rearrangement was investigated.(3) Synthesis of methylenecyclopropane spiro linked with cycloalkanes via cyclization of allylic epoxides was investigated, its application to a sythesis of fused rings 3-methylfuranes.2. Diastereoselective cyclization of omega-formylated allylic silanes into bicyclic alpha-methylene-gamma-lactones.(1) Diastereoselective cyclization of omega-formylated allylic silanes using chiral auxiliary groups was investigated.(2) Diastereoselective sythesis of cis and trans-p-methanolides starting from (+)-citronellal was sucessful.(3) Total synthesis of cembrenolide, marine natural product, was successful.