Regiospecific formation of sugar-derived ketonitrone towards unconventional C-branched pyrrolizidines and indolizidines?
Organic & Biomolecular Chemistry Pub Date: 2019-07-08 DOI: 10.1039/C9OB01419E
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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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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