Stereo- and regioselective glycosylations to the bis-C-arylglycoside of kidamycin.
In explorations toward the total synthesis of the antitumor anthrapyran natural product kidamycin, the regioselective introduction of aminosugars angolosamine and vancosamine as C-arylglycosides has been accomplished onto hydroxylated anthrapyran aglycones. Specifically, the 9,11-dihydroxylated anthrapyran A undergoes sequential glycosylations with angolosamine synthon B and vancosamine synthon C to regio- and stereoselectively afford bis-C-glycoside D corresponding to the C-glycoside pattern of kidamycin.
Fei
ZhongBo
Z
Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.
McDonald
Frank E
FE
D000617:Aminoglycosides / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D006031:Glycosylation; D015394:Molecular Structure; D013237:Stereoisomerism
D000617:Aminoglycosides; D000970:Antineoplastic Agents; D006027:Glycosides; C100062:kidamycin
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