Preparation of (4S)-4-hydroxy-3-methyl-2-(2′-propynyl)-2-cyclopentenone by combination of enzymatic hydrolysis and chemical transformation

Abstract

(4S)-4-Hydroxy-3-methyl-2-(2′-propynyl)-2-cyclopentenone ((S)-2), which is an important alcohol moiety of optically active pyrethroid insecticides, was prepared from the corresponding racemic acetate ((±)- 1) by the combination of enzymatic hydrolysis and chemical transformation in high chemical and optical yields.