Tripyrrolic prodigiosenes, derivatives of the natural product prodigiosin, have been produced via multi-step synthesis beginning with 2-formyl pyrroles bearing various functionalities at the 4-position. Two tin complexes are also reported, and these feature a prodigiosene ligand bearing a conjugated benzyl-ester. Antimicrobial activities of prodigiosenes are evaluated against Gram positive and Gram negative bacterial strains, as well as a yeast.