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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 ?-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.

SUBMITTER: Qi C

PROVIDER: S-EPMC5890919 | biostudies-literature | 2018 Feb

REPOSITORIES: biostudies-literature

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

Qi Chao C Wang Wenyu W Reichl Kyle D KD McNeely James J Porco John A JA

Angewandte Chemie (International ed. in English) 20180129 8

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<sup>II</sup> -catalyzed dehydrogenative coupling. Further studies employing asymmetric nucleophilic epoxidation indicate that the atropisomers of aurofusarin and derivatives are not configurationally stable at ambient temperature. ...[more]

PMID: 29318760

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