Novel analogues of Troger's base were prepared regioselectively from 4-amino-N-methylpyrrole carboxylates in good yield. Catalytic hydrogenation of dibenzyl-4,9-methano-1,6-dimethyl-4,5,9,10-tetrahydro-1H,6H-dipyrrolo-[3,2-b :3',2'-f][1,5]diazocin-2,7-dicarboxylate 2b led to 4,9-methano-1,6-dimethyl-4,5,9,10-tetrahydro-1H,6H-dipyrrolo-[3,2-b:3',2'-f] [1,5]diazocin-2,7-dicarboxylic acid 3 which was used for the preparation of Troger's base derivatives of natural antibiotics via an amide protocol. The novel heterocyclic Troger's bases were characterized by a variety of spectroscopic techniques and compound 2b by X-ray crystallography. Incorporation of guanidine as the terminal group in the N-methylpyrrole Troger's base skeleton opens the possibility for preparation of water soluble derivatives.