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  • Title: A short synthesis of (+)-cyclophellitol.
    Author: Hansen FG, Bundgaard E, Madsen R.
    Journal: J Org Chem; 2005 Nov 25; 70(24):10139-42. PubMed ID: 16292857.
    Abstract:
    [reaction: see text] A new synthesis of (+)-cyclophellitol, a potent beta-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.
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