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Paper | Regular issue | Vol 43, No. 10, 1996, pp.2131-2138
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7522
Synthesis of 2- or/and 6-Methylated Analogues of Isoguvacine (1,2,3,6-Tetrahydropyridine-4-carboxylic Acid) a GABAA Agonist

Markus Rohr, Saïd Chayer, Fabrice Garrido, André Mann, Maurizio Taddei, and Camille-Georges Wermuth

*Laboratoire de Pharmacochimie Moleculaire, (UPR 421 DU CNRS), Centre de Neurochimie du CNRS, 5, rue Blaise Pascal, 67084 Strasbourg-Cedex, France


1,2,3,6-tetrahydropyridine-4-carboxylic acid (isoguvacine) and related 2-and/or 6-methylated analogues (1-4) were synthesized using the methoxycarbonylation [Pd(OAc)2, PPh3, CO, MeOH)] of their corresponding vinylic triflates. Analogue (5), the 6-methyl-1,2,3,6-tetrahydropyridine-4-carboxylic acid was obtained after a reductive deoxygenation of the corresponding β-keto ester.