Total Synthesis of the Marine Alkaloid Palau'amine

摘要

The architecturally intriguing marine alkaloid palau'amine (1) posed an inspiring structural and synthetic challenge to chemists since its first isolation in 1993 by Scheuer and coworkers. The structure that was originally proposed for palau'amine—involving a ds-fused azabicyclo[3.3.0]octane structure and epimeric at C17—lured many synthetic groups into despair. Although this structure was certainly chemically reasonable, the isolation of additional congeners combined with detailed NMR and computational analyses suggested a structural revision of palau'amine to the structure shown for 1. In a recent Communication, Baran and coworkers described the successful preparation of the revised structure of palau'amine (1) in totally synthetic form, and thus delivered further evidence for the revised structure. Therefore, the endeavors of many research groups towards the first total synthesis of this unique natural product have now culminated in this achievement.