Herein, we describe our efforts culminating in the total syntheses of discoipyrroles A, B, and C in 6, 6, and 7 steps respectively with excellent overall yield. Total syntheses of these unique natural products have been accomplished involving microwave-mediated Paal-Knorr pyrrole synthesis, Pd-catalyzed carbonylative transformation, and MoOPH (Vedejs reagent) oxidation as key reactions to construct the 1,2,3,5-tetrasubstituted pyrrole and oxidative cyclization of highly substituted pyrrole as key steps.