American Chemical Society
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A Concise Approach to Anthraquinone–Xanthone Heterodimers

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journal contribution
posted on 2018-04-05, 00:00 authored by Stephen D. Holmbo, Sergey V. Pronin
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.