Total Synthesis of (−)-Lepenine

Abstract

The first asymmetric total synthesis of lepenine has been accomplished. The synthesis features a tethered intramolecular Diels-Alder reaction, an intramolecular Mannich reaction, and a Diels-Alder reaction between an ortho-quinone monoketal and ethylene, resulting in stereoselective construction of the unique hexacyclic system.