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Synthesis of the branched C-glycoside substructure of altromycin B.

ABSTRACT: Tungsten-catalyzed cycloisomerization of alkynyl alcohols including 8 provides only the endocyclic enol ether (11) as a key intermediate for the branched C-glycoside substructure (2) of altromycin B. A sequence of Stille cross-coupling reaction and regio- and stereoselective functional group transformations affords each C13-diastereomer of the branched C-arylglycoside (2a and 2b). [reaction: see text]

SUBMITTER: Koo B

PROVIDER: S-EPMC1388186 | biostudies-literature | 2005 Aug

REPOSITORIES: biostudies-literature

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Synthesis of the branched C-glycoside substructure of altromycin B.

Koo Bonsuk B McDonald Frank E FE

Organic letters 20050801 17

Tungsten-catalyzed cycloisomerization of alkynyl alcohols including 8 provides only the endocyclic enol ether (11) as a key intermediate for the branched C-glycoside substructure (2) of altromycin B. A sequence of Stille cross-coupling reaction and regio- and stereoselective functional group transformations affords each C13-diastereomer of the branched C-arylglycoside (2a and 2b). [reaction: see text] ...[more]

PMID: 16092834

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