Alternative route to carbacyclin using lipase-catalysed enantioselective hydrolysis of methyl 8-acetoxybicyclo[4.3.0]non-3-ene-7-carboxylate

Abstract

Pseudomonas fluorescens lipase was found to catalyse the hydrolysis of the racemic acetate methyl 8-acetoxybicyclo [4.3.0] non -3-ene-7-carboxylate 4 in a highly enantioselective fashion to provide the optically active (–)-methyl 8-hydroxybicyclo[4.3.0]non-3-ene-7-carboxylate (–)-3. This compound was easily converted into a bicyclo [3.3.0] octane derivative, methyl 3-acetoxy-7-oxobicyclo[3.3.0]octane- 2-carboxylate 8, an intermediate in the synthesis of carbacyclin 1.