Journal article
A Short Synthesis of (+)-Cyclophellitol
A new synthesis of (+)-cyclophellitol, a potent b-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.
Language: | English |
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Year: | 2005 |
Pages: | 10139-10142 |
ISSN: | 15206904 and 00223263 |
Types: | Journal article |
DOI: | 10.1021/jo051645q |
ORCIDs: | Madsen, Robert |