Enantiopure piperidines via stereoselective Ireland–Claisen rearrangement: entry into corynanthe alkaloids

Abstract

A fully stereo-divergent Ireland–Claisen rearrangement of achiral lactones has been developed, enabling access to all four possible stereoisomers of 3,4-disubstituted piperidines and pyrrolidines. The utility of these building blocks has been showcased in the total synthesis of meroquinene ester and cardioprotective indole alkaloids sitsirikine and dihydrositsirikine.