Enantioselective Total Synthesis of (+)-Gephyrotoxin 287C

Gephyrotoxin 287C, a bioactive alkaloid bearing a perhydropyrrolo[1,2-a]quinoline skeleton with five stereocenters, is an attractive target for synthetic organic chemistry. We achieved an enantioselective total synthesis of (+)-gephyrotoxin 287C, for which the key steps were palladium-catalyzed asymmetric allylic amination using a chiral diaminophosphine oxide (DIAPHOX) preligand, diastereoselective intramolecular Mannich reaction, and tin tetrachloride-catalyzed diastereoselective conjugate addition/protonation.