Synthesis of (-)-N-Acetylcolchinol

Significance

N-Acetylcolchinol is a potent tubulin polymerization inhibitor, which is in clinical trials for tumor suppression. It is typically derived from degradation of Colchicine. This first asymmetric synthesis exploits a highly enantioselective addition of a binaphthol-modified alkynylboronate to an N-acetylimine to generate the single stereogenic center.