A Short Synthesis of (+)-Cyclophellitol

Flemming Gundorph Hansen, Eva Bundgaard, Robert Madsen

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

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.
Original languageEnglish
JournalJournal of Organic Chemistry
Volume70
Issue number24
Pages (from-to)10139-10142
ISSN0022-3263
DOIs
Publication statusPublished - 2005

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