Asymmetric synthesis of (+)- and (-)-batyl alcohol, a key synthetic intermediate for platelet-activating factor, by using biocatalysts.

Abstract

Asymmetric synthesis of platelet-activating factor (PAF) and its enantiomer by using biocatalysts was studied. Microbial reduction of the pro-chiral α-ketoester (3) afforded (+) -4 (> 99% ee), which could be converted to (+) -and (-) -batyl alcohol (12), a key synthetic intermediate for PAF. Compound (-) -4 (96% ee), with the requisite configuration for the synthesis of natural PAF, could also be obtained by enzyme-catalyzed enantioselective hydrolysis of (±) -15.