Synthesis of novel indole-based ring systems by acid-catalyzed condensation from a -amino aldehydes and L-Trp-OMe

Acid-catalysed condensation of tryptophan with different alpha-amino aldehyde derivatives has been explored as a useful route to the synthesis of novel amino acid derived heterocycles and peptidomimetic scaffolds. By this approach, compounds containing a tetrahydro-beta-carboline and a novel octahydropyrrolo[3',2':3,4]pyrrolo[2,3-b]indole system have been efficiently synthesized. Here we report the characterization of these new compounds and preliminary studies of the reactivity of the tetrahydro-beta-carboline system.