A new divergent asymmetric synthesis of (+)- and (-)-ethosuximides and their anti-convulsant activities

Authors
Katoh, T Nishide, K Node, M Ogura, H
Citation
T. Katoh et al., A new divergent asymmetric synthesis of (+)- and (-)-ethosuximides and their anti-convulsant activities, HETEROCYCLE, 50(2), 1999, pp. 833-841
Citations number
27
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
50
Issue
2
Year of publication
1999
Pages
833 - 841
Database
ISI
SICI code
0385-5414(19990401)50:2<833:ANDASO>2.0.ZU;2-2
Abstract
Both enantiomers of ethosuximide were synthesized divergently from nitroole fin lactone [(-)-2a] or [(-)-2b], which was obtained by asymmetric nitroole fination of alpha-methyl-gamma-butyrolactone with chiral nitro enamines der ived from L-proline. Although anticonvulsant activity was confirmed in both enantiomers, the (S)-ethosuximide was more active than the (R)-enantiomer.