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On the proposed structures and stereocontrolled synthesis of the cephalosporolides.

ABSTRACT: The synthesis of four candidate stereoisomers of cephalosporolide H is described, made possible by a zinc-chelation strategy for controlling the stereochemistry of oxygenated 5,5-spiroketals. The same strategy likewise enables the first stereocontrolled synthesis of cephalosporolide E, which is typically isolated and prepared admixed with its spiroketal epimer, cephalosporolide F.

SUBMITTER: Tlais SF

PROVIDER: S-EPMC3458751 | biostudies-literature | 2012

REPOSITORIES: biostudies-literature

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On the proposed structures and stereocontrolled synthesis of the cephalosporolides.

Tlais Sami F SF Dudley Gregory B GB

Beilstein journal of organic chemistry 20120814

The synthesis of four candidate stereoisomers of cephalosporolide H is described, made possible by a zinc-chelation strategy for controlling the stereochemistry of oxygenated 5,5-spiroketals. The same strategy likewise enables the first stereocontrolled synthesis of cephalosporolide E, which is typically isolated and prepared admixed with its spiroketal epimer, cephalosporolide F. ...[more]

PMID: 23019461

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