Facile Synthesis of Fused Oxasapphyrins

A simple rapid synthetic route is developed to synthesize new fused meso-aryl oxasapphyrins in 8–10% yield using easily accessible 3-benzoylpyrrole as the key precursor. The method involves McMurry coupling of 3-benzoylpyrrole to obtain an E/Z mixture of dipyrroethene, which was subjected to benzoylation followed by NaBH4 reduction to afford dipyrroethene diol in situ that was then condensed with 16-oxatripyrrane under mild acid-catalyzed conditions to afford fused oxasapphyrins.