Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5225392 | Tetrahedron | 2007 | 6 Pages |
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.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Ganesh Pandey, Shrinivas G. Dumbre, Sujit Pal, M. Islam Khan, M. Shabab,