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1,3-dipolar cycloaddition reaction of D-glucose-derived nitrone with allyl alcohol: Synthesis of 2-hydroxy-1-deoxycastanospermine analogues
- Source :
- Journal of Organic Chemistry. Feb 18, 2005, Vol. 70 Issue 4, 1356-1363
- Publication Year :
- 2005
-
Abstract
- The synthesis and evaluation of glycosidase inhibitory activity of polyhydroxylated indolizidine alkaloids namely 2-hydroxy-1-deoxycastanospermine and 2-hydroxyl-1-deoxy-8a-epi-castano-spermine is reported. The key step involves the intermolecular 1,3-dipolar cycloaddition of allyl alcohol to D-glucose derived nitrone, followed by tosylation that afforded four diastereomeric sugar-substituted isoxazolidines with the desired regioselectivity.
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 70
- Issue :
- 4
- Database :
- Gale General OneFile
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- edsgcl.132731245