Tetrahedron letters

Highly stereoselective synthesis of substituted hydrindanes related to the antiepileptic drug topiramate

MN Greco, BE Maryanoff

Index: Greco, Michael N.; Maryanoff, Bruce E. Tetrahedron Letters, 1992 , vol. 33, # 35 p. 5009 - 5012

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Citation Number: 25

Abstract

Abstract Multistep syntheses of two “carbocyclic” analogues 2 and 3 of topiramate (1) were effected with excellent stereocontrol. Two key reactions employed were: deoxygenation- rearrangement of an enone with p-tosylhydrazine and catecholborane (14--> 15 and 5--> 7) and face-selective vicinal dihydroxylation with OsO 4 (viz. 15--> 16 and 8--> 9).