Issue 3, 2004
From the journal:

Chemical Communications

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

John Fawcett,a   Gerry A. Griffiths,a   Jonathan M. Percy,*a   Stéphane Pintat,‡a   Clive A. Smith,c   Neil S. Spencerb  and  Emi Uneyamaa  

* Corresponding authors

a Department of Chemistry, University of Leicester, University Road, Leicester, UK
E-mail: jmp29@le.ac.uk
Fax: +44 116 252 3789
Tel: +44 116 252 2140

b School of Chemical Sciences, University of Birmingham, Edgbaston, Birmingham, UK

c GlaxoSmithKline Pharmaceuticals, New Frontiers Science Park, Third Avenue, Harlow, UK

Abstract

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.

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

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Article information

DOI
https://doi.org/10.1039/B313813E
Article type
Communication
Submitted
31 Oct 2003
Accepted
03 Dec 2003
First published
05 Jan 2004

Chem. Commun., 2004, 302-303

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

J. Fawcett, G. A. Griffiths, J. M. Percy, S. Pintat, C. A. Smith, N. S. Spencer and E. Uneyama, Chem. Commun., 2004, 302 DOI: 10.1039/B313813E

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