SHORT CHIRAL SYNTHESES OF MORPHINAN AND RELATED SYSTEMS

Abstract

Morphine and its derivatives continue to challenge the creativity of synthetic chemists. The aim of this research is to execute a short chiral synthesis of the morphinan system. Chirality is introduced via asymmetric reduction; the key step is the formation of four rings- the tetracyclic phenanthrofuran by an intramolecular Diels-Alder cycloaddition. The fifth ring was completed by three different methods, and three different pentahydrophenanthrofuran systems were obtained.