Synthesis of highly functionalized pyrrolidines as tunable templates for the direct access to (±)-coerulescine and the tricyclic core of martinellines

An aza-Michael induced ring closure (aza-MIRC) tandem reaction of benzyl (2-bromoethyl) carbamate with various Michael acceptors is described. The N-Cbz-beta-gem-disubstituted pyrrolidines thus obtained were proved to be versatile intermediates for the rapid access to both martinelline and spirooxindole backbones. An application of this strategy towards an expedient 4 step total synthesis of (+/-)-coerulescine is also presented.