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Issue 29, 2019
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Regiospecific formation of sugar-derived ketonitrone towards unconventional C-branched pyrrolizidines and indolizidines

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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).

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

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Publication details

The article was received on 24 Jun 2019, accepted on 06 Jul 2019 and first published on 08 Jul 2019


Article type: Paper
DOI: 10.1039/C9OB01419E
Org. Biomol. Chem., 2019,17, 7066-7077

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

    F. Massicot, G. Messire, A. Vallée, J. Vasse, S. Py and J. Behr, Org. Biomol. Chem., 2019, 17, 7066
    DOI: 10.1039/C9OB01419E

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