38 生体触媒を用いるキラルシントンの合成とその天然物合成への応用

概要

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In the field of the synthesis of polyoxoantibiotics or the related polyfunctional natural products, the use of chiral synthon is quite advantageous. We now report the synthesis of optically active 3-hydroxy-2-methyl propionate derivative I, based on the asymmetric reduction including immobilized microorganisms with prepolymer and kinetical resolution with industrialized enzyme (lipase). 1. Determination of absolute structure of (-)-oudemansin B (1) (-)-oudemansin B was synthesized from the two different chiral synthons, hydroxy lactone 5a and (2R,3S)-epoxy ester 20b obtained by microbial asymmetric chiral induction method. Natural product was found to possess the 9S, 10S absolute configuration. 2. Asymmetric reduction with immobilized microbial cells by prepolymer method Asymmetric reduction of 2-methyl 3-oxopropionate derivative II with immobilized microbial cells was carried out. It was found that by proper selection of prepolymer in the stage of immobilization, chemical and optical yields were improved significantly compared with the use of native microorganisms. 3. Highly enantioselective hydrolyses of 3-hydroxy or acetoxy 2-methyl esters with industrialized lipase Highly enantioselective hydrolyses of 3-hydroxy or acetoxy 2-methyl esters with lipase Candida cylindracea MY-50, lipase "Amano A" and lipase "Amano A-6" isolated from Aspergillus niger, are described.
天然有機化合物討論会の論文
1986-09-09