Alam, Mohammad Abrar ; Kumar, Amit ; Vankar, Yashwant D. (2008) Total synthesis of L-(+)-Swainsonine and other indolizidine azasugars from D-glucose European Journal of Organic Chemistry, 2008 (29). pp. 4972-4980. 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.200800649
Abstract
A total synthesis of L-(+)-swainsonine, a potent and specific inhibitor of naringinase, along with the syntheses of six unnatural indolizidine azasugars are reported by starting from D-glucose. L-(+)-Swainsonine was synthesized in 14 steps in 17 % overall yield. Further, two of the indolizidine analogues were found to be good glycosidase inhibitors at micromolar concentrations. In all of these syntheses, the key step was an intramolecular SN2 reaction.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to John Wiley and Sons. |
| Keywords: | Nitrogen Heterocycles; Azasugars; Epoxides; Nucleophilic Substitution |
| ID Code: | 58169 |
| Deposited On: | 31 Aug 2011 06:41 |
| Last Modified: | 31 Aug 2011 06:41 |
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