Total Synthesis of Cribrostatin IV:  Fine-Tuning the Character of an Amide Bond by Remote Control

Abstract

We report the enantioselective total synthesis of cribrostatin IV (1). Key features of this synthesis involve the convergent coupling of two highly functionalized homochiral components followed by a "lynchpin" Mannich cyclization to establish the pentacyclic core (cf. 19 --> 20).