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Intramolecular 5-endo-Trig Aminomercuration of β-Hydroxy-γ-alkenylamines: Efficient Route to a Pyrrolidine Ring and Its Application for the Synthesis of (+)-Castanospermine and Analogues

Authors :
Dilip D. Dhavale
Vaishali S. Shinde
Shankar D. Markad
Narayan S. Karanjule
Source :
The Journal of Organic Chemistry. 71:4667-4670
Publication Year :
2006
Publisher :
American Chemical Society (ACS), 2006.

Abstract

The intramolecular aminomercuration reaction of sugar-derived beta-hydroxy-gamma-alkenylamines 8a-c undergoes 5-endo-trig cyclization in high yield. The sugar-substituted pyrrolidines thus obtained were elaborated to the synthesis of polyhydroxylated indolizidine alkaloids, namely, castanospermine 1a, 1-epi-castanospermine 1b, and 8a-epi-castanospermine 1c, having promising glycosidase inhibitory activities.

Details

ISSN :
15206904 and 00223263
Volume :
71
Database :
OpenAIRE
Journal :
The Journal of Organic Chemistry
Accession number :
edsair.doi.dedup.....b4ec823e0fb7548e71e1de82f3f023c6
Full Text :
https://doi.org/10.1021/jo0601617