Regiospecific formation of sugar-derived ketonitrone towards unconventional C-branched pyrrolizidines and indolizidines
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).
Références
- Titre
- Regiospecific formation of sugar-derived ketonitrone towards unconventional C-branched pyrrolizidines and indolizidines
- Type de publication
- Article de revue
- Année de publication
- 2019
- Auteurs
- Massicot, Fabien, Messire Gatien, Vallée Alexis, Vasse Jean-Luc, Py Sandrine, and Behr Jean-Bernard
- Revue
- Org. Biomol. Chem.
- Volume
- 17
- Ticket
- 29
- Pagination
- 7066–7077
Soumis le 3 septembre 2019