Ring-Junction-Substituted Polyhydroxylated Pyrrolizidines and Indolizidines from Ketonitrone Cycloadditions - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2018

Ring-Junction-Substituted Polyhydroxylated Pyrrolizidines and Indolizidines from Ketonitrone Cycloadditions

Résumé

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.

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Chimie
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Dates et versions

hal-01846977 , version 1 (23-07-2018)

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Citer

Evelyn Lieou Kui, Alice Kanazawa, Jean-Bernard Behr, Sandrine Py. Ring-Junction-Substituted Polyhydroxylated Pyrrolizidines and Indolizidines from Ketonitrone Cycloadditions. European Journal of Organic Chemistry, 2018, 2018 (19), pp.2178 - 2192. ⟨10.1002/ejoc.201800212⟩. ⟨hal-01846977⟩
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