Synthesis of novel polyhydroxylated pyrrolidine–triazole/-isoxazole hybrid molecules?
Organic & Biomolecular Chemistry Pub Date: 2014-12-09 DOI: 10.1039/C4OB01934B
Abstract
A straightforward synthesis of novel, 2-heterocyclyl polyhydroxylated pyrrolidines is described. Stereocontrolled additions of nucleophiles to cyclic nitrones generated the corresponding 2,3-trans adducts, allowing the synthesis of the corresponding pyrrolidines via key intermediates bearing an alkyne and a nitrile oxide. Three hybrid systems, including a pyrrolidine with two isoxazoles and one triazole, are efficiently prepared via 1,3-dipolar cycloaddition. Biological testing of the product alkaloids showed that subtle structural variations have drastic effects on their inhibitory activities against glucosidases.
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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