Total synthesis of aurofusarin: studies on the atropisomeric stability of bis-naphthoquinones
Files
Accepted manuscript
Date
2018-02-19
Authors
Qi, Chao
Wang, Wenyu
Reichl, Kyle D.
McNeely, James
Porco, John A.
Version
OA Version
Citation
Chao Qi, Wenyu Wang, Kyle D Reichl, James McNeely, John A Porco. 2018. "Total Synthesis of Aurofusarin: Studies on the Atropisomeric Stability of Bis-Naphthoquinones.." Angew Chem Int Ed Engl, Volume 57, Issue 8, pp. 2101 - 2104.
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 PdII -catalyzed dehydrogenative coupling. Further studies employing asymmetric nucleophilic epoxidation indicate that the atropisomers of aurofusarin and derivatives are not configurationally stable at ambient temperature.