Application of Microorganisms and Enzymes to the Synthesis of Chiral Cyclopentane and Bicyclo [3.3.0] octane Derivatives

Abstract

Optically active cyclopentane and bicyclo [3.3.0] octane derivatives were synthesized by utilizing biochemical methods. Pseudomonas fluorescens lipase was found to be an effective enzyme for the enantioselective hydrolysis of monoacetoxy-and diacetoxycyclopentanes such as (±) -4a, (±) -5a, (±) -6a, and 7a. However, hydrolysis of bicyclo [3.3.0] octane trans-acetate ((±) -8a) using this enzyme resulted in low enantioselectivity. Optically pure (+) -8b for the synthesis of carbacyclin was obtained from (+) -8a by using porcine pancreatic lipase. Reduction of 3-acetyl-7-oxobicyclo [3.3.0] -oct-2-ene with baker's yeast afforded a useful intermediate ((+) -11b) for the synthesis of hirsutic acid.