Synthesis of Novel Indole-Based Ring Systems by Acid-Catalysed Condensation from α-Amino Aldehydes and L-Trp-OMe

Acid‐catalysed condensation of tryptophan with different α‐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‐β‐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‐β‐carboline system.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008) Compounds containing a tetrahydro‐β‐carboline and a novel octahydropyrrolo[3′,2′:3,4]pyrrolo[2,3‐b]indole system have been efficiently synthesized by acid‐catalysed condensation of tryptophan with different α‐amino aldehyde derivatives. Here we report the characterization of these new compounds and preliminary studies of the reactivity of the tetrahydro‐β‐carboline system.