Enantioselective Syntheses of the Alkaloids <i>cis</i>-195A (Pumiliotoxin C) and <i>trans</i>-195A Based on Multiple Applications of Asymmetric Catalysis

Abstract

Short enantio- and diastereoselective syntheses of the decahydroquinoline alkaloids <i>cis</i>- (pumiliotoxin C) and <i>trans</i>-<b>195A</b> are presented. Key steps are an enantioselective iridium-catalyzed allylic amination, a Suzuki–Miyaura coupling, a catalyst-controlled copper-catalyzed 1,4-addition, and a reductive amination