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- Title
Total Synthesis of Aurofusarin: Studies on the Atropisomeric Stability of Bis‐Naphthoquinones.
- Authors
Qi, Chao; Wang, Wenyu; Reichl, Kyle D.; McNeely, James; Porco, Jr., John A.
- Abstract
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.
- Subjects
HYDROCARBON synthesis; ATROPISOMERS; NAPHTHOQUINONE; ANNULATION; QUINONE; CONDENSATION reactions
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 8, p2123
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201711535