Literature DB >> 29318760

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

Chao Qi1, Wenyu Wang1, Kyle D Reichl1, James McNeely1, John A Porco1.   

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.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

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

Mesh：

Substances：

Year:  2018        PMID： 29318760      PMCID： PMC5890919          DOI： 10.1002/anie.201711535

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


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