Cycloadditions of Sugar-Derived Nitrones Targeting Polyhydroxylated Indolizidines
Authors: Martella D., D’Adamio G., Parmeggiani C., Cardona F., Moreno-Clavijo E., Robina I., Goti A.
Autors Affiliation: Univ Florence, Dept Chem Ugo Schiff, Via Lastruccia 3-13, I-50019 Sesto Fiorentino, FI, Italy; CNR INO UOS Sesto Fiorentino, Via N Carrara 1, I-50019 Sesto Fiorentino, FI, Italy; LENS, Via N Carrara 1, I-50019 Sesto Fiorentino, FI, Italy; Univ Seville, Fac Quim, Dept Quim Organ, C Prof Garcia Gonzalez 1, E-41012 Seville, Spain
Abstract: 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 alpha-mannosidases depends on the configuration at C-2 of the indolizidine moiety.
Journal/Review: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume: 2016 (8) Pages from: 1588 to: 1598
KeyWords: Cycloaddition; Diastereoselectivity; Carbohydrates; Nitrogen heterocycles; Nitrones; InhibitorsDOI: 10.1002/ejoc.201501427Citations: 22data from “WEB OF SCIENCE” (of Thomson Reuters) are update at: 2023-02-05References taken from IsiWeb of Knowledge: (subscribers only)Connecting to view paper tab on IsiWeb: Click hereConnecting to view citations from IsiWeb: Click here