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

Title1,3-Dipolar cycloaddition reaction of D-glucose-derived nitrone with allyl alcohol: synthesis of 2-hydroxy-1-deoxycastanospermine analogues
Publication TypeJournal Article
Year of Publication2005
AuthorsKaranjule, NS, Markad, SD, Sharma, T, Sabharwal, SG, Puranik, VG, Dhavale, DD
JournalJournal of Organic Chemistry
Volume70
Issue4
Pagination1356-1363
Date PublishedFEB
Type of ArticleArticle
ISSN0022-3263
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.

DOI10.1021/jo048176x
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

4.785

Divison category: 
Center for Material Characterization (CMC)
Physical and Materials Chemistry