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Ring‐Junction‐Substituted Polyhydroxylated Pyrrolizidines and Indolizidines from Ketonitrone Cycloadditions
Author(s) -
Lieou Kui Evelyn,
Kanazawa Alice,
Behr JeanBernard,
Py Sandrine
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800212
Subject(s) - chemistry , regioselectivity , cycloaddition , ring (chemistry) , nitrogen atom , stereochemistry , 1,3 dipolar cycloaddition , organic chemistry , combinatorial chemistry , catalysis
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.