Pandey, Ganesh ; Dumbre, Shrinivas G. ; Pal, Sujit ; Islam Khan, M. ; Shabab, M. (2007) Synthesis and evaluation of 1-deoxy-8-epi-castanospermine, 1-deoxy-8-hydroxymethyl castanospermine, and (6S,7S,8R,8aR)-8-amino-octahydroindolizine-6,7-diol Tetrahedron, 63 (22). pp. 4756-4761. ISSN 0040-4020
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Official URL: http://www.sciencedirect.com/science/article/pii/S...
Related URL: http://dx.doi.org/10.1016/j.tet.2007.03.085
Abstract
A short, versatile, and enantioselective synthesis of 1-deoxy-8-epi-castanospermine (5), 1-deoxy-8-hydroxymethyl castanospermine (6), and (6S,7S,8R,8aR)-8-amino-octahydroindolizine-6,7-diol (7) is achieved from a common template 12. The key step utilized is PET provoked amine radical cyclization of 11 to 12 in excellent diastereoselectivity. The exocyclic double bond at C-8 of the template is functionalized to obtain 5-7 as exclusive diastereomers. 1-Deoxy-8-epi-castanospermine exhibited inhibition of α- and β-galactosidase and β-glucosidase. Compounds 6 and 7 were found to be weak inhibitors of β-glucosidase.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | 1-Deoxy-8-epi-castanospermine; Castanospermine; Glycosidase Inhibitors |
| ID Code: | 61021 |
| Deposited On: | 13 Sep 2011 11:30 |
| Last Modified: | 13 Sep 2011 11:30 |
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