Karanjule, Narayan S. ; Markad, Shankar D. ; Shinde, Vaishali S. ; Dhavale, Dilip D. (2006) Intramolecular 5-endo-trig aminomercuration of β-hydroxy-γ-alkenylamines: efficient route to a pyrrolidine ring and its application for the synthesis of (+)-castanospermine and analogues Journal of Organic Chemistry, 71 (12). pp. 4667-4670. ISSN 0022-3263
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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo0601617
Related URL: http://dx.doi.org/10.1021/jo0601617
Abstract
The intramolecular aminomercuration reaction of sugar-derived β-hydroxy-γ-alkenylamines 8a-c undergoes 5-endo-trig cyclization in high yield. The sugar-substituted pyrrolidines thus obtained were elaborated to the synthesis of polyhydroxylated indolizidine alkaloids, namely, castanospermine 1a, 1-epi-castanospermine 1b, and 8a-epi-castanospermine 1c, having promising glycosidase inhibitory activities.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 75339 |
| Deposited On: | 22 Dec 2011 13:12 |
| Last Modified: | 22 Dec 2011 13:12 |
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