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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
- 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