Stereoselective synthesis of 2-amino-3-fluoro bicyclo[3.1.0]hexane-2,6-dicarboxylic acid.
(+)-2-Aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (LY354740) is a conformationally restricted glutamate analogue that is a potent, selective and orally active group 2 metabotropic glutamate receptor agonist possessing anticonvulsant and anxiolytic properties. Herein, we describe a stereoselective and highly efficient synthesis of its 3-beta fluoro derivative using the Corey-Link methodology to create the amino acid stereogenic center.
Pedregal
Concepción
C
Centro de Investigación Lilly, SA, Avda. de la Industria, 30, 28108, Alcobendas, Madrid, Spain. pedregal_concepcion@lilly.com
Prowse
William
W
D001671:Biochemistry / Q000379:methods*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D003510:Cyclohexanes / Q000138:chemical synthesis*; D003998:Dicarboxylic Acids; D013237:Stereoisomerism
D001643:Bridged Bicyclo Compounds; D003510:Cyclohexanes; D003998:Dicarboxylic Acids; C418123:MGS 0008; C104753:eglumetad