Synthesis of Carba-β-l-Fructopyranose and Carbacyclic Analogs of Topiramate, an Anticonvulsant Agent

We have prepared carba-p-L-fructopyranose (3) starting from (1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylic acid (5). In addition, an unsaturated derivative bearing a double bond in the ring (viz. 4) was prepared. These L-carbacyclic derivatives of fructose were converted to the corresponding analogs of topiramate, a novel anticonvulsant agent currently in clinical practice.