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Cycloadditions of Sugar‐Derived Nitrones Targeting Polyhydroxylated Indolizidines
Author(s) -
Martella Daniele,
D'Adamio Giampiero,
Parmeggiani Camilla,
Cardona Francesca,
MorenoClavijo Elena,
Robina Inmaculada,
Goti Andrea
Publication year - 2016
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.201501427
Subject(s) - indolizidine , chemistry , nitrone , cycloaddition , moiety , stereochemistry , glycoside hydrolase , alkene , pyrroline , 1,3 dipolar cycloaddition , pyrrolizidine , organic chemistry , enzyme , catalysis , alkaloid
The 1,3 dipolar cycloaddition reactions of three pentose‐derived pyrroline N ‐oxides with mono‐ and disubstituted alkenes are reported. A strong dependence of the diastereoselectivity of the cycloadditions on the relative configuration of the nitrone stereocentres was observed. Further transformation of the reaction products allowed the synthesis of four new tetrahydroxylated indolizidines. Their activity as glycosidase inhibitors was evaluated against a panel of commercially available glycosidases. The specificity of inhibitory activity against amyloglucosidase and α‐mannosidases depends on the configuration at C‐2 of the indolizidine moiety.