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Paper | Special issue | Vol 50, No. 2, 1999, pp.833-841
Published online, 1st January, 1970
DOI: 10.3987/COM-98-S(H)78
A New Divergent Asymmetric Synthesis of (+)- and (-)-Ethosuximides and Their Anti-Convulsant Activities

Takahiro Katoh, Kiyoharu Nishide, Manabu Node,* and Hiroo Ogura

*Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8414, Japan


Both enantiomers of ethosuximide were synthesized divergently from nitroolefin lactone [(-)-2a] or [(-)-2b], which was obtained by asymmetric nitroolefination of α-methyl-γ-butyrolactone with chiral nitro enamines derived from L-proline. Although anticonvulsant activity was confirmed in both enantiomers, the (S)-ethosuximide was more active than the (R)-enantiomer.