In summary, we have described the serendipitous isolation a novel isoporphyrinoid -calixcorrole -via DDQ-mediated oxidative addition of two pyrrole molecules to meso-tris(p-methylphenyl)corrole. The product was obtained as two separable diastereomers with a combined yield of 46.6%. The molecular constitution (i.e., connectivity) was fully elucidated with 2D NMR analysis, but in the absence so far of a crystal structure (in spite of many attempts to obtain one and considerable experience with structure determination in the corrole field ), the stereochemistry of the two diastereomers remains unresolved. Also, somewhat disappointingly, our preliminary attempts at metal insertion into calixcorrole have proved unsuccessful. Although copper appears to insert (as evidenced by MS), the complexes proved unstable and demetallated in the course of isolation. Gold also failed to insert via the 'acetate method'. In spite of the setbacks, we view the discovery of calixcorrole as a significant development. The compound may lend itself to applications involving molecular recognition such as anion sensing and sugar sensing. Also, the synthetic strategy may prove useful elsewhere in porphyrin analogue chemistry, and help in the creation of new isoporphyrinoids with interesting and useful properties. Time will tell.