Synthesis of Functionalized
Bicyclic Precursors of Heptulosonic Acid Analogues

Hatim Filali; Stéphanie Ballereau; Fouad Ouazzani Chahdi; Michel Baltas

doi:10.1055/s-0028-1083301

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Synthesis 2009(2): 251-256
DOI: 10.1055/s-0028-1083301

PAPER

Synthesis of Functionalized Bicyclic Precursors of Heptulosonic Acid Analogues

Hatim Filali^a,b, Stéphanie Ballereau^a, Fouad Ouazzani Chahdi^b, Michel Baltas*^a
^a Laboratoire de Synthèse et Physicochimie de Molécules d’Intérêt Biologique, UMR-CNRS 5068, Université de Toulouse, UPS, 31062 Toulouse Cedex 9, France
Fax: +33(5)61556011; e-Mail: baltas@chimie.ups-tlse.fr;
^b Laboratoire de Chimie Organique Appliquée, Faculté des Sciences et Techniques de Fès, BP 2202 Fès, Morocco

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Publication History

Received 2 September 2008
Publication Date:
09 January 2009 (online)

Abstract
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Abstract

The synthesis of novel bicyclic functionalized precursors of heptulosonic acids is described. The reactivity of the C4 position was studied and allowed the synthesis of 4-deoxy-4-iodo, 4-azido-4-deoxy, 4-amino-4-deoxy, and 4-deoxy-4-fluoro bicyclic derivatives.

Key words

bicyclic compounds - fluorine - halogenation - azides - carbohydrates

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