Abstract An efficient, optimized, and scalable process for the synthesis of C-ring ester- functionalized prodigiosenes has been developed by (i) exploiting a silylative Mukaiyama aldol strategy for the condensation of alkyl 5-formyl-2, 4-dimethylpyrrole-3-carboxylate and 4- methoxy-3-pyrrolin-2-one to form the corresponding ester-functionalized dipyrrinone analogues, and (ii) developing a facile synthesis of stable bromodipyrrin analogues for the ...