Abstract The total synthesis of prodigiosin (1), possessing the characteristic pyrrolylpyrromethene skeleton of a class of naturally-occurring polypyrroles, is detailed, The approach is based on the application of an inverse electron demand Diels-Alder reaction of dimethyl 1, 2, 4, 5-tetrazine-3, 6-dicarboxylate in a 1, 2, 4, 5-teirazine→ 1, 2-diazine→ pyrrole strategy for preparation of prodigiosin pyrrole ring B and the subsequent ...