A novel and enantioselective synthesis of d-(+)-biotin via a Sharpless asymmetric dihydroxylation strategy

A novel and enantioselective synthesis of d-(+)-biotin has been accomplished starting from commercially available cyclohexanone. The key steps in the sequence are the Sharpless asymmetric dihydroxylation of a (E)-ethyl 3-(2-chlorocyclohex-1-en-1-yl)acrylate derivative to establish the stereocenters of d-(+)-biotin, the carboxyalkyl side chain is introduced by unmasking the cyclohexene by ozonolysis and enzymatic hydrolysis of a thioacetate.