Teneraic acid (piperidine-2,6-dicarboxylic acid) is a naturally occurring imino acid that comprises three stereoisomers due to its two asymmetric centers at C2 and C6. The configuration of natural teneraic acid is reported to correspond to trans -(2 S ,6 S ). However, a few studies are focused on the stereospecific synthesis of trans -(2 S ,6 S )-teneraic acid. The present study investigates a convenient synthetic method that includes regiospecific anodic oxidation and stereospecific cobalt-catalyzed carbonylation to obtain trans -(2 S ,6 S )-teneraic acid. Methyl ( S )- N -benzoyl-α-methoxypipecolate, the key intermediate that displays a structure that corresponds to an intermediate ( N -α-hydroxyalkyl amide) of intramolecular amidocarbonylation, was obtained via an anodic oxidation of methyl ( S )- N -benzoylpipecolate. Subsequently, cobalt-catalyzed carbonylation converted the methyl ( S )- N -benzoyl-α-methoxypipecolate to trans -(2 S ,6 S )- N -benzoyl-teneraic acid dimethyl ester in good optical purity (>95% enantiomeric excess (ee)) and modest yield (63%). Finally, de-protection occurred via acidic hydrolysis to obtain trans -(2 S ,6 S )-teneraic acid. The stereochemistry of synthesized teneraic acid was confirmed as corresponding to trans -(2 S ,6 S ) by comparing its physical properties with those of a cis-meso -isomer and those of a trans -(2 S ,6 S )-isomer that were reported in previous studies.