STEREOSPECIFIC SYNTHESIS OF (1S,3R)-1-AMINOCYCLOPENTANE-1,3-DICARBOXYLIC ACID, A SELECTIVE AGONIST OF METABOTROPIC GLUTAMATE RECEPTORS

Authors
MA DW MA JY DAI LX
Citation
Dw. Ma et al., STEREOSPECIFIC SYNTHESIS OF (1S,3R)-1-AMINOCYCLOPENTANE-1,3-DICARBOXYLIC ACID, A SELECTIVE AGONIST OF METABOTROPIC GLUTAMATE RECEPTORS, Tetrahedron : asymmetry, 8(6), 1997, pp. 825-827
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
6
Year of publication
1997
Pages
825 - 827
Database
ISI
SICI code
0957-4166(1997)8:6<825:SSO(>2.0.ZU;2-F
Abstract
(1S,3R)-Aminocyclopentane-1,3-dicarboxylic acid 1, a widely used metab otropic glutamate receptor agonist has been synthesized. Hydrolysis fo llowed by Curtius rearrangement of 5 derived from dimethyl (S)-malate gave 6 with excellent diastereofacial selectivity (> 97% de), which wa s converted into 1 through an S(N)2 reaction of mesylate 7 with tetrae thylammonium cyanide. (C) 1997 Elsevier Science Ltd.