Organic & Biomolecular Chemistry 2015-02-21

Synthesis of novel polyhydroxylated pyrrolidine-triazole/-isoxazole hybrid molecules.

Cheng-Kun Lin, Li-Wei Cheng, Huang-Yi Li, Wen-Yi Yun, Wei-Chieh Cheng

Index: Org. Biomol. Chem. 13(7) , 2100-7, (2015)

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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.