This dissertation deals with the synthesis of novel bioactive derivatives of the natural occurring hymenialdisine. As a part of this project, a solvent-free, efficient, and easy to handle diversification strategy for annulated hymenialdisine-type bisindoles was developed. A C-C bond-formation reaction on activated silica under mild reaction conditions starting from aziridines, epoxides or hydroxyl compounds is the key technology. The versatility of different aziridines as key building blocks was demonstrated with H-, O-, and N-nucleophiles in a diversity oriented synthesis to build up a focused chemical library. Furthermore, novel transition metal mediated introduction and transformation of functional-groups for potential application in the synthesis of novel drug candidates were developed.
