Carbaporphyrins have been shown to have many unusual properties, including the ability to form organometallic derivatives under mild conditions.  However, little work has been conducted on the related di- or tricarbaporphyrinoid systems.  A new approach to di- and tricarbaporphyrinoids related to the benziporphyrins is under investigation.  Indene enamine 1 was condensed with benzene aldehydes in the presence of dibutylboron triflate to give the novel fulvene aldehydes 2 in good yields.  Similarly, benzene dialdehydes reacted with 1 to afford the tripyrrene analogues 3.  Current investigations are being directed at the construction of porphyrin-like macrocycles from these precursors using the “2+2” and “3+1” MacDonald approaches.  The properties of these compounds will provide insights into the stability and aromaticity of carbaporphyrinoids.