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Total Synthesis and Structural Determination of the Dimeric Tetrahydroxanthone Ascherxanthone A

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posted on 29.03.2017, 21:29 by Zheming Xiao, Yayue Li, Shuanhu Gao
The first total synthesis of the dimeric tetrahydroxanthone ascherxanthone A has been accomplished. This synthetic strategy features (1) enantioselective intramolecular allylic C–H oxidation to construct a core chiral chromane, (2) intramolecular aldol reaction/dehydration to form the enone group, and (3) intermolecular Suzuki–Miyaura coupling to connect two monomeric tetrahydroxanthones. This synthetic work allowed us to determine the axial chirality of the 2,2′-biaryl C–C bond and the absolute configuration of the ascherxanthone A. This approach should facilitate the preparation of derivatives and structurally related natural products for medicinal studies.