Ajish Kumar, K. S. ; Chaudhari, Vinod D. ; Puranik, Vedavati G. ; Dhavale, Dilip D. (2007) Synthesis and glycosidase inhibitory studies of pentahydroxyindolizidines: D-glucose-derived aziridine-2-carboxylate approach European Journal of Organic Chemistry, 2007 (29). pp. 4895-4901. ISSN 1434-193X
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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/ejoc.20...
Related URL: http://dx.doi.org/10.1002/ejoc.200700461
Abstract
D-Glucose-derived aziridine-2-carboxylate 1 was converted into α-amino aldehyde 7, which, after Wittig olefination, asymmetric dihydroxylation, hydrogenation followed by LiAlH4 reduction, and N-Cbz protection, afforded two diastereomeric pyrrolidines 11a and 11b with sugar appendages. Removal of the 1,2-acetonide functionality in 11a/11b and reductive amination gave the pentahydroxyindolizidine alkaloids 6g and 6h, respectively, with (S) absolute configurations at the ring junctions. The glycosidase inhibitory activities of these compounds were studied.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to John Wiley and Sons, Inc. |
| Keywords: | Iminosugars; Indolizidine; Asymmetric Dihydroxylation (AD); N-methylmorpholine N-oxide (NMO) |
| ID Code: | 9738 |
| Deposited On: | 02 Nov 2010 10:45 |
| Last Modified: | 31 May 2011 11:51 |
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