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- Title
Ring‐Junction‐Substituted Polyhydroxylated Pyrrolizidines and Indolizidines from Ketonitrone Cycloadditions.
- Authors
Lieou Kui, Evelyn; Kanazawa, Alice; Behr, Jean‐Bernard; Py, Sandrine
- Abstract
A 1,3‐dipolar cycloaddition reaction of carbohydrate‐derived five‐membered cyclic ketonitrones with alkynes and alkenes was developed as an efficient and regioselective process to access highly functionalised isoxazolines and isoxazolidines bearing a quaternary centre α to the nitrogen atom. The latter compounds were used as intermediates for the synthesis of unprecedented ring‐junction‐substituted polyhydroxylated pyrrolizidines and indolizidines. These compounds were evaluated against a panel of glycosidases, and showed moderate but selective inhibition of α‐glucosidases.
- Subjects
PYRROLIZIDINES; INDOLIZIDINES; RING formation (Chemistry); NITRONES; ALKENES; ALKYNES; REGIOSELECTIVITY (Chemistry)
- Publication
European Journal of Organic Chemistry, 2018, Vol 2018, Issue 19, p2178
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201800212