Preliminary steps in the synthesis of "congressane 63" (pentacyclotetradecane) have been studied. Methods have been investigated to prepare the starting material, 1,4-cyclohexadione, its ethylene glycol-monoketal, and the initial products of the synthesis. The latter include the eneamine, bicyclo acrolein adduct, and the pyrolysis elimination of the amine group. The acrolein addition and the pyrolysis have yet to be satisfactorily performed.