Synthesis of (2S,2'R,3'R)-2-(1'[3H],2',3'-Dicarboxylcyclopropyl)-glycine ([3H]-DCG-IV)

Article abstract of DOI:10.1002/(SICI)1099-1344(200001)43:1<1::AID-JLCR285>3.0.CO;2-N

The conformationally restricted analog of L-glutamic acid (L-Glu, 1), (2S,2'R,3'R)2-(2',3'-dicarboxylcyclopropyl)-glycine (DCG-IV, 2) is a potent group II mGluR agonist. In order to study the distribution of group IImGluRs in the brain and to establish a radioligand binding assay we have developed a synthesis of [³H]-DCG-IV (2a). The key intermediate, α-bromo aldehyde 7, was prepared in four steps starting from (-)-Feist's acid (3). The incorporation of tritium was performed by reaction of 7 with tri-n-butyltin tritide to give 8, which was transformed in two steps into 2a.