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C-Aryl glycosides via tandem intramolecular benzyne-furan cycloadditions. Total synthesis of vineomycinone B2 methyl ester.

ABSTRACT: A triply convergent total synthesis of vineomycinone B2 methyl ester has been achieved by an approach with a longest linear sequence of 16 steps. The synthesis features the use of silicon tethers as disposable linkers to control the regiochemistry in two tandem Diels-Alder reactions of substituted benzynes and glycosyl furans to provide rapid access to the fully intact anthrarufin core of vineomycinone B2 methyl ester.

SUBMITTER: Chen CL

PROVIDER: S-EPMC2525791 | biostudies-literature | 2006 Oct

REPOSITORIES: biostudies-literature

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C-Aryl glycosides via tandem intramolecular benzyne-furan cycloadditions. Total synthesis of vineomycinone B2 methyl ester.

Chen Chi-Li CL Sparks Steven M SM Martin Stephen F SF

Journal of the American Chemical Society 20061001 42

A triply convergent total synthesis of vineomycinone B2 methyl ester has been achieved by an approach with a longest linear sequence of 16 steps. The synthesis features the use of silicon tethers as disposable linkers to control the regiochemistry in two tandem Diels-Alder reactions of substituted benzynes and glycosyl furans to provide rapid access to the fully intact anthrarufin core of vineomycinone B2 methyl ester. ...[more]

PMID: 17044691

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