Carbaporphyrinoid systems such as azuliporphyrin have attracted a great deal of attention in recent years due to their unique reactivity and spectroscopic properties.  However, prior to this work, related structures with two adjacent carbocyclic subunits were unknown.  In order to generate the required precursor dialdehyde 1, azulene dialdehyde 2 was reacted with indene enamine 3 in the presence of dibutylboron triflate.  Subsequent “2 + 2” MacDonald condensation of fulvene 1 with dipyrrylmethane 4 in the presence of TFA afforded the borderline aromatic carbaazuliporphyrin 5 in good yields.