Total Synthesis of Cyclophellitol from L-Quebrachitol

Abstract
Cyclophellitol [1L-(1,3/2,4,5,6)-4,5-epoxy-6-(hydroxy-methyl)cyclohexane-1,2,3-triol] , a ß-glucosidase inhibitor, has been synthesized enantiospecifically from a naturally abundant cyclitol, L-quebrachitol (1L-2-O-methyl-chiro-inositol), via a Peterson olefination and an aluminum trichloride-tetrabutylammonium iodide mediated demethylation.

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