title: Total Synthesis and Structural Determination of the Dimeric Tetrahydroxanthone Ascherxanthone A.
abstract: 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.
authors.affiliation: Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University , 3663N Zhongshan Road, Shanghai 200062, China.
authors.forename: Zheming
authors.initials: Z
authors.lastname: Xiao
authors.affiliation: Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University , 3663N Zhongshan Road, Shanghai 200062, China.
authors.forename: Yayue
authors.initials: Y
authors.lastname: Li
authors.affiliation: Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University , 3663N Zhongshan Road, Shanghai 200062, China.
authors.forename: Shuanhu
authors.identifier: 0000-0001-6919-4577
authors.initials: S
authors.lastname: Gao
mesh_terms: D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D044004:Xanthones / Q000737:chemistry*
chemical_list: D044004:Xanthones; C502715:ascherxanthone A