Bande, Omprakash P. ; Jadhav, Vrushali H. ; Puranik, Vedavati G. ; Dhavale, Dilip D. (2007) 1,3-dipolar cycloaddition reaction of a D-galactose derived nitrone with allyl alcohol: synthesis of polyhydroxylated perhydroazaazulene alkaloids Tetrahedron: Asymmetry, 18 (10). pp. 1176-1182. ISSN 0957-4166
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S09574...
Related URL: http://dx.doi.org/10.1016/j.tetasy.2007.05.012
Abstract
Diastereofacial intermolecular 1,3-dipolar cycloaddition of D-galactose derived nitrone with allyl alcohol followed by tosylation afforded, in a 1:1 ratio endo- and exo-isooxazolidines 4a and 4b with complete diastereoselectivity at the nitrone carbon. The N-O bond reductive cleavage and S2 displacement afforded the pyrrolidine ring with a galactose appendage that on acetonide cleavage and reductive amino-cyclization afforded pentahydroxylated perhydroazaazulenes 1a and 1b.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 9608 |
| Deposited On: | 02 Nov 2010 11:47 |
| Last Modified: | 31 May 2011 11:51 |
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