Three kinds of fused porphyrinoids, L2-L4, possessing different types of corrole-based frameworks were synthesized from a pyrrole-substituted corrole isomer (norrole L1). Oxidation of L1 afforded a unique N-Cmeso -fused pyrrolyl isonorrole L2, involving the fusion of an auxiliary pyrrolic NH moiety with a meso-sp(3) -hybridized carbon atom. Subsequently, L2 underwent macrocycle transformations to give singly and doubly N-CAr -fused N-confused corroles, L3 and L4, respectively. L3 and L4 contain fused [18.104.22.168]-tetra- and [22.214.171.124.6.5]-hexacyclic structures, respectively, prepared through lateral annulation. These skeletal transformation reactions from norrole to its isomer isonorrole and finally to N-confused corrole indicate that multiply fused porphyrinoids could be readily synthesized from pyrrole-appended confused porphyrinoids.