Total synthesis of (−)-incarvilline and (−)-incarvillateine

An enantioselective, concise total synthesis of (−)-incarvilline and (−)-incarvillateine has been achieved in longest linear 9 steps (24.3% overall yield) and in 11 steps (16.5% overall yield) from (−)-carvone, respectively. The present synthesis features a notable Favorskii rearrangement of the O-protected chlorohydrin derivative of (−)-carvone to construct four of the five contiguous stereocenters on the bicyclic piperidine moiety and DMAP-catalyzed esterification of incarvilline with α-truxillic acid anhydride to generate incarvillateine skeleton.