A Concise Approach to Anthraquinone–Xanthone Heterodimers

A synthetic approach to anthraquinone–xanthone heterodimers is described. The route to the pentacyclic core features an efficient assembly of a benzocycloheptenone via a new intramolecular oxidative arylation of an enol ether and a Hauser–Kraus annulation–aldol reaction sequence to access the charac...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2018-04, Vol.140 (15), p.5065-5068
Main Authors: Holmbo, Stephen D, Pronin, Sergey V
Format: Article
Language:English
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Summary:A synthetic approach to anthraquinone–xanthone heterodimers is described. The route to the pentacyclic core features an efficient assembly of a benzocycloheptenone via a new intramolecular oxidative arylation of an enol ether and a Hauser–Kraus annulation–aldol reaction sequence to access the characteristic bicyclo[3.2.2]­nonene motif. Acremoxanthone A is synthesized in 10 steps from commercially available material to demonstrate the application of this approach.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.8b03110