The first total synthesis of 4-deoxyannomontacin

Abstract

A convergent enantioselective total synthesis of 4-deoxyannomontacin, a newly isolated and characterized acetogenin compound which shows very high cytotoxicity, has been synthesized enantioselectively via 17 reaction steps with an overall yield of 15%. The four stereogenic centers near the ethereal link are derived from D-glucose and introduced using Sharpless asymmetric dihydroxylation. The chiral carbon in the butenolide moiety is taken from ethyl (S)-lactate whereas the hydroxy-group configuration is obtained from salenCo^III-catalyzed hydrolytic kinetic resolution.