Asymmetric synthesis of (-)-6-epi-centrolobine

A stereoselective total synthesis of (-)-6-epi-centrolobine, an unnatural analogue of (-)-centrolobine, starting from readily available tri-O-acetyl-D-glucal has been described for the first time. The key steps involved in this synthetic approach are stereoselective C-glycosidation, dehydroxylation and Wittig reaction. The target molecule was achieved in nine steps with 49% overall yield.