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Synlett 2004(12): 2095-2098  
DOI: 10.1055/s-2004-831305
LETTER
© Georg Thieme Verlag Stuttgart · New York

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

Michael H. Parker*, Bruce E. Maryanoff, Allen B. Reitz
Johnson & Johnson Pharmaceutical Research and Development, L.L.C. Welsh and McKean Roads, P.O. Box 0776, Spring House, PA 19477-0776, USA
Fax: +1(215)6284985; e-Mail: mparker@prdus.jnj.com;
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Publication History

Received 25 May 2004
Publication Date:
26 August 2004 (online)

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Abstract

We have prepared carba-β-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.

Key words

carbocycles - carbohydrates - stereoselective synthesis - anticonvulsant agents - dihydroxylations

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