Total Synthesis of Aurofusarin: Studies on the Atropisomeric Stability of Bis-Naphthoquinones

Abstract

An efficient annulation involving pyrone addition to a quinone and Dieckmann condensation was developed for rapid assembly of a γ-naphthopyrone monomeric precursor to the bis-naphthoquinone natural product aurofusarin. Dimerization was achieved through Pd^II -catalyzed dehydrogenative coupling. Further studies employing asymmetric nucleophilic epoxidation indicate that the atropisomers of aurofusarin and derivatives are not configurationally stable at ambient temperature.

Keywords: annulation; axial chirality; dehydrogenative coupling; epoxidation; naphthoquinones.