Total Synthesis and Structural Determination of the
Dimeric Tetrahydroxanthone Ascherxanthone A
Posted on 2017-03-29 - 21:29
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.
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Xiao, Zheming; Li, Yayue; Gao, Shuanhu (2017). Total Synthesis and Structural Determination of the
Dimeric Tetrahydroxanthone Ascherxanthone A. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.7b00592
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AUTHORS (3)
ZX
Zheming Xiao
YL
Yayue Li
SG
Shuanhu Gao
KEYWORDS
intramolecularbiarylSuzukienantioselectiveallylicchiralitystrategyenone groupapproachmonomeric tetrahydroxanthonessynthesisoxidationaldoldimeric tetrahydroxanthone ascherxanthonederivativeconfigurationStructural Determinationcore chiral chromaneTotal SynthesispreparationDimeric Tetrahydroxanthone Ascherxanthonebond