Stereoselective solid-phase synthesis of a triaza tricyclic ring system: Anew chemotype for lead discovery

Sequential pyrrolidine and hydantoin ring-forming reactions have been appli ed in the stereoselective solid-phase synthesis of a conformationally const rained, tricyclic triazacyclopenta[c]pentalene scaffold, These novel compou nds share the structural complexity characteristic of certain alkaloid natu ral products and represent a source of chemical diversity that complements more traditional classes of heterocyclic compounds of interest as potential pharmaceutical agents. They are assembled in a 12-step reaction sequence f rom 4 variable building blocks by combining an intramolecular azomethine yl ide cycloaddition reaction with a final cyclative cleavage from resin.