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 anth...

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Bibliographic Details
Published in:Organic letters 2007-08, Vol.9 (18), p.3547-3550
Main Authors: Fei, ZhongBo, McDonald, Frank E
Format: Article
Language:English
Subjects:
Aminoglycosides - chemistry
Antineoplastic Agents - chemistry
Glycosides - chemistry
Glycosylation
Molecular Structure
Stereoisomerism
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol7014219