The syntheses of 7,13-dimethyl[3.2]metacyclophan-10-ene (5) and 7,10,11,13-tetramethyl[3.2]metacyclophan-10-ene (6) starting from 1,3-bis(4-methylphenyl)propane (1) are reported. 5 exists in the anti conformation typical of [3.2]metacyclophan-enes while 6 prefers the syn conformation because of steric repulsion between the methyl groups at the etheno bridge and at the aromatic rings.