Enantioselective synthesis of the (+)-anti-7,8-dihydrodiol-9,10-epoxide of the potent carcinogen benzo[a]pyrene

Abstract

The title compound, the most important genotoxic metabolite of benzo[a]pyrene, has been prepared efficiently in a synthesis which capitalized on Jacobsen-type enantioselective epoxidation of 9,10-dihydrobenzo[a]pyrene, cleavage of the epoxide by KOH–Me₂SO to give the tetrahydro-trans-7,8-diol, and formation of the dibenzoate from which the contaminating antipode was removed by crystallization.