Although a smaller-scale test reaction (~10 mg corrole, 2 eq DDQ, and 40 eq pyrrole in dichloromethane) at 100 °C revealed calixcorrole as the main product after ~15 h, a subsequent normal-scale reaction (~50 mg corrole, 2 eq DDQ, and 40 eq pyrrole in dichloromethane) at the same temperature yielded only a 15.3% combined, isolated yield of calixcorrole. In the end, our best conditions for a normal-scale reaction consisted of refluxing ~50 mg of corrole in dichloromethane with 3 eq DDQ and 13 eq pyrrole for about 2 days. Following work-up, the isolated yields were 12.6 % for F1 and 34.0% for F2, corresponding to a combined yield of 46.6%.