The investigation, development, and implementation of two azadiene Diels-Alder reactions for the preparation of the two identical monomeric 1,2-dihydro-3H- pyrrolo[3.2-e]indole units (right-hand and central segments, PDE I/II) and the unusual cyclopropylpyrroloindole unit (left-hand segment) of CC-1065 (NSC 298233), the most potent antitumor-antibiotic isolated to date, are described.