A Diels–Alder approach to trans-trisbicyclo[2.2.1]heptabenzene derivative

A new route to the synthesis of a trans-tris(bicyclo[2.2.1]hexeno)benzene derivative, using Diels–Alder reaction as critical step, was investigated. The compound with six methoxycarbonyl groups was successfully synthesized in good yield without any organometallic reagents. Some useful by-products from dimethyl but-2-ynedioate were also isolated from the last step. Perhaps due to stereo-hindrance or electrostatic repulsion in the cis-isomer, trans-isomer was found to be the only isomer in the crystal and its structure was proved by X-ray diffraction.