Bande, Omprakash P. ; Jadhav, Vrushali H. ; Puranik, Vedavati G. ; Dhavale, Dilip D. (2009) Highly diastereoselective 1,3-dipolar cycloaddition of a D-galactose-derived nitrone with dimethyl maleate: synthesis of polyhydroxylated perhydroaza-azulenes Synlett, 12 . pp. 1959-1963. ISSN 0936-5214
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Official URL: https://www.thieme-connect.com/ejournals/abstract/...
Related URL: http://dx.doi.org/10.1055/s-0029-1217541
Abstract
An intermolecular 1,3-dipolar cycloaddition of a D-galactose-derived nitrone with dimethyl maleate was found to be perfectly diastereoselective at the nitrone carbon to give exclusive formation of isoxazolidine. The N-O bond reductive cleavage in isoxazolidine followed by lactam reduction afforded a pyrrolidine ring skeleton with sugar appendage that on acetonide cleavage and reductive amino-cyclization gave hitherto unknown hydroxy-methyl-substituted hexa- and pentahydroxy perhydroazaazulenes.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Thieme Medical Publishers. |
| Keywords: | 1,3-dipolar Nitrone Olefin Cycloaddition (DNOC); Nitrone; Iminosugars; Inhibitors; Diastereoselectivity |
| ID Code: | 75331 |
| Deposited On: | 22 Dec 2011 13:13 |
| Last Modified: | 22 Dec 2011 13:13 |
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