The synthesis of a cocaine intermediate via a sodium–liquid ammonia carbon–carbon σ-bond cleavage of an azabicyclic succinate-type ester

Abstract

A four-step synthesis of the diester (1), based on the sodium–liquid ammonia reductive cleavage of the carbon–carbon σ-bond of the bicyclic compound (2) is described; since (1) has previously converted into (±)-cocaine (3), the overall synthetic pathway constitutes a total synthesis of this alkaloid.