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Article dans une revue

Regiospecific formation of sugar-derived ketonitrone towards unconventional C -branched pyrrolizidines and indolizidines

Abstract : The synthesis of unprecedented branched pyrrolizidines and indolizidines was accomplished via nitrone chemistry. The required ketonitrone, a known intermediate usually obtained as a mixture of regioisomers, was prepared in a pure form from D-arabinose by a sequence of oximation/reduction/oxidation steps. Nucleophilic vinylation or allylation followed by ring-closing metathesis of the corresponding N-allylpyrrolidines furnished the targeted iminosugars, which proved potent and selective inhibitors of alpha-glucosidase from rice (GH31 family).
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https://hal.univ-grenoble-alpes.fr/hal-02402766
Contributeur : Sandrine Py <>
Soumis le : mardi 10 décembre 2019 - 15:53:07
Dernière modification le : mercredi 14 octobre 2020 - 03:53:45

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Fabien Massicot, Gatien Messire, Alexis Vallée, Jean-Luc Vasse, Sandrine Py, et al.. Regiospecific formation of sugar-derived ketonitrone towards unconventional C -branched pyrrolizidines and indolizidines. Organic and Biomolecular Chemistry, Royal Society of Chemistry, 2019, 17 (29), pp.7066-7077. ⟨10.1039/c9ob01419e⟩. ⟨hal-02402766⟩

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