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Stereo- and regioselective glycosylations to the bis-C-arylglycoside of kidamycin.

ABSTRACT: 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.

SUBMITTER: Fei Z

PROVIDER: S-EPMC4604443 | biostudies-literature | 2007 Aug

REPOSITORIES: biostudies-literature

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Stereo- and regioselective glycosylations to the bis-C-arylglycoside of kidamycin.

Fei ZhongBo Z McDonald Frank E FE

Organic letters 20070811 18

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 ...[more]

PMID: 17691798

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