Towards conformationally-locked difluorosugar analogues: an unexpected sense of dihydroxylation

Difluorinated cyclooctenones, synthesised using RCM, can be used as templates for stereoselective oxidative transformations to products that undergo transannular reactions to afford conformationally-locked analogues of 2-deoxy-2,2-difluorosugars with different stereochemical relationships between th...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2004-02 (3), p.302-303
Main Authors: Fawcett, John, Griffiths, Gerry A, Percy, Jonathan M, Pintat, Stéphane, Smith, Clive A, Spencer, Neil S, Uneyama, Emi
Format: Article
Language:English
Subjects:
Carbohydrate Conformation
Cyclization
Deoxy Sugars - chemistry
Fluorine - chemistry
Hydroxylation
Stereoisomerism
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Summary:Difluorinated cyclooctenones, synthesised using RCM, can be used as templates for stereoselective oxidative transformations to products that undergo transannular reactions to afford conformationally-locked analogues of 2-deoxy-2,2-difluorosugars with different stereochemical relationships between the C-2 and C-3 hydroxyl groups.
ISSN:1359-7345
DOI:10.1039/b313813e