A Nine-Step Enantioselective Total Synthesis of (−)-Vincorine

摘要

A concise and highly enantioselective total synthesis of the akuammiline alkaloid (−)-vincorine has been accomplished. A key element of the synthesis is a stereoselective organocatalytic Diels–Alder, iminium cyclization cascade sequence, which serves to construct the tetracyclic alkaloid core architecture in one step from simple achiral precursors. The challenging seven-membered, azepanyl ring system is installed by way of a single electron-mediated cyclization event initiated from an acyl telluride precursor. The total synthesis of (−)-vincorine is achieved in nine steps and 9% overall yield from commercially available starting materials.