Synthesis of novel polyhydroxylated pyrrolidine–triazole/-isoxazole hybrid molecules. Issue 7 (19th December 2014)

• Record Type: Journal Article
• Authors: Lin, Cheng-Kun; Cheng, Li-Wei; Li, Huang-Yi; Yun, Wen-Yi; Cheng, Wei-Chieh
• Is Part Of: Organic & biomolecular chemistry. Volume 13:Issue 7(2015)
• Page Start: 2100
• Page End: 2107
• Publication Date: 2014-12-19
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c4ob01934b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A straightforward synthesis of novel, 2-heterocyclyl polyhydroxylated pyrrolidines is described. 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.