Efficient Strategy for the Construction of Both Enantiomers of the Octahydropyrroloquinolinone Ring System: Total Synthesis of (+)-Aspidospermidine.

An efficient and highly stereoselective intramolecular [3 + 2] cycloaddition of nonstabilized azomethine ylide generated from a designed bicyclic aminal precursor is reported for the synthesis of both (-)- and (+)-octahydropyrroloquinolinone. One of the enantiomers is further advanced to accomplish the total synthesis of (+)-aspidospermidine.