In this work we developed new approaches to three different classes of compounds. In the first chapter we employed PIFA as an oxidant to develop a direct route to pyrrolobenzodiazepines. We also developed a new way to generate acyl radicals by oxidative decarboxylation. The utility of this methodology was shown in the synthesis of 8-deoxy DC-81. In the second chapter we developed a five-step synthetic route to 1,4-phenanthrenequinones. We also used one of these phenanthrenequinones for the construction of an angularly-fused aromatic systems. In the third chapter we studied Lewis acid-mediated cyclizations of acyl quinones. We synthesized a precursor that may be used in the preparation of substituted morphinanes.