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A Short Synthesis of (+)-Cyclophellitol.
- Source :
-
Journal of Organic Chemistry . 11/25/2005, Vol. 70 Issue 24, p10139-10142. 4p. 5 Diagrams. - Publication Year :
- 2005
-
Abstract
- A new synthesis of (+)-cyclophellitol, a potent β-glucosidase inhibitor, has been completed in nine steps from D-xylose. The key transformations involve a zinc-mediated fragmentation of benzyl-protected methyl 5-deoxy-5-iodo-xylofuranoside followed by a highly diastereoselective indium-mediated coupling with ethyl 4-bromocrotonate. Subsequent ring-closing olefin metathesis, ester reduction, olefin epoxidation, and deprotection then afford the natural product. This constitutes the shortest synthesis of (+)-cyclophellitol reported to date. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 70
- Issue :
- 24
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 19240547
- Full Text :
- https://doi.org/10.1021/jo051645q