Synthesis of 2-or/and 6-methylated analogues of isoguvacine (1,2,3,6-tetrahydropyridine-4-carboxylic acid) a GABAA agonist

Article abstract of DOI:10.3987/com-96-7522

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.