Back to Search Start Over

1,3-dipolar cycloaddition reaction of D-glucose-derived nitrone with allyl alcohol: Synthesis of 2-hydroxy-1-deoxycastanospermine analogues

Authors :
Karanjule, Narayan S.
Markad, Shankar D.
Sharma, Tarun
Sabharwal, Sushma G.
Puranik, Vedavati G.
Dhavale, Dilip D.
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