Pseudomonas sp. NOF-5による (±)-イソプレゴールの光学分割について

概要

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In biochemical resolution of (±)-isopulegyl acetate diastereomers with Pseudomonas sp. NOF-5, (-)-isopulegyl and (-)-isoisopulegyl acetate were hydrolyzed stereospecifically, but their enantiomers were unreactive. (±)-Neoisopulegyl acetate was not hydrolyzed by this method. (±)-Isopulegyl chloroacetate was hydrolyzed faster than its acetate with the same microorganism in high substrate concentration (ca. 50%) to obtain (-)-isopulegol and (+)-isopulegyl chloroacetate. The industrial production of (-)-citronellol from (±)-isopulegyl chloroacetate was also investigated. (±)-Isopulegyl chloroacetate was prepared in high yield by transesterification of (±)-isopulegol and methyl chloroacetate in the presence of aluminum isopropoxide as catalyst. (+)-Isopulegol obtained from (±)-isopulegyl chloroacetate by the described biochemical resolution followed by basic hydrolysis was thermally decomposed by vapor-phase reaction at 590_??_600°C to quantitative yield (-)-citronellal. Catalytic hydrogenation of (-)-citronellal gave (-)-citronellal gave (-)-citronellol.
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