Total Synthesis of Aurofusarin: Studies on the Atropisomeric Stability of Bis‐Naphthoquinones |
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| Authors: | Dr. Chao Qi Dr. Wenyu Wang Dr. Kyle D. Reichl Dr. James McNeely Prof. Dr. John A. Porco Jr. |
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| Affiliation: | Department of Chemistry and Center for Molecular Discovery (BU-CMD), Boston University, Boston, MA, USA |
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| 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. |
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| Keywords: | annulation axial chirality epoxidation dehydrogenative coupling naphthoquinones |
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