Karanjule, Narayan S. ; Markad, Shankar D. ; Sharma, Tarun ; Sabharwal, Sushma G. ; Puranik, Vedavati G. ; Dhavale, Dilip D. (2005) 1,3-dipolar cycloaddition reaction of D-glucose-derived nitrone with allyl alcohol: synthesis of 2-hydroxy-1-deoxycastanospermine analogues Journal of Organic Chemistry, 70 (4). pp. 1356-1363. ISSN 0022-3263
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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo048176x
Related URL: http://dx.doi.org/10.1021/jo048176x
Abstract
The synthesis and evaluation of glycosidase inhibitory activity of polyhydroxylated indolizidine alkaloids namely 2-hydroxy-1-deoxycastanospermine 3a,b and 2-hydroxy-1-deoxy-8a-epi-castanospermine 3c,d is reported. The key step involves the intermolecular 1,3-dipolar cycloaddition of allyl alcohol to d-glucose-derived nitrone 4, followed by tosylation, that afforded four diastereomeric sugar-substituted isoxazolidines 5a-d with the desired regioselectivity. The one-pot conversion of 5a-d to pyrrolidines 8a-d by hydrogenolysis, removal of 1,2-acetonoide functionality, and hydrogenation afforded corresponding target molecules 3a-d.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 75343 |
| Deposited On: | 22 Dec 2011 13:12 |
| Last Modified: | 22 Dec 2011 13:12 |
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