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Synthèse de C-aryl glycosides par voie intramoléculaire

Abstract : C-Aryl glycosides are attractive natural products exhibiting a wide range of antibiotic and
antitumor activities. These compounds are challenging synthetic targets, which require the
availability of a stereo- and regioselective C-glycosylation method.
We have developed a new, stereocontrolled synthesis of C-aryl glycosides based on the
intramolecular reactions of 2-0-benzylated pentenyl glycosides. This strategy was applied to the
synthesis of Bergenine derivatives. Some unexpected cyclisations were observed in the
mannopyranoside series.
In order to generalise the strategy, we have investigated several tethers between a sugar
and an aromatic moiety: we have found that glucosides carrying 2-O-arylsilyl substituents gave
exclusively the corresponding αlpha-C-aryl glucosides thus providing the first method of
stereocontrolled synthesis of C-aryl glycosides in this configuration.
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Submitted on : Tuesday, August 28, 2007 - 4:53:35 PM
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  • HAL Id : tel-00168483, version 1


Cyril Rousseau. Synthèse de C-aryl glycosides par voie intramoléculaire. Autre. Université d'Orléans, 2002. Français. ⟨tel-00168483⟩



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