Three epimers of ethylene glycol bis(tropane-3-carboxylate) (3alpha,3alpha'-, 3alpha,3beta'-, 3beta,3beta'-) have been synthesized by starting from 3-tropinone. 3-Tropinone was converted into the corresponding enol triflate and then subjected to palladium-catalyzed alkoxycarbonylation to provide the key intermediate methyl trop-2-ene-3-carboxylate in good yield. Stereoselective routes were developed to afford the three stereoisomers of ethylene glycol bis(tropane-3-carboxylate).