Total Synthesis of (−)-Kaitocephalin Based on a Rh-Catalyzed C–H Amination

Abstract

A total synthesis of (−)-kaitocephalin, an ionotropic glutamate receptor antagonist, is accomplished in highly stereocontrolled manner via Overman rearrangement, rhodium-catalyzed benzylic C–H amination, pyrrolidine formation involving nucleophilic opening of a cyclic sulfamate, and rhodium-catalyzed allylic C–H amination as key steps