title: Copper-catalyzed cyclization of iodo-tryptophans: a straightforward synthesis of pyrroloindoles.
abstract: Pyrroloindoles are a key structural motif found in a wide number of biologically active alkaloids. Intramolecular copper-catalyzed coupling of readily accessible 2-iodo-tryptophan derivatives occurs in excellent yield, affording a wide range of polysubstituted, enantioenriched tetrahydropyrrolo[2,3- b]indoles. Diketopiperazines are also suitable substrates for this cyclization reaction, which affords a straightforward entry to tetra- to hepta-polycyclic systems.
authors.affiliation: Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles Saint-Quentin en Yvelines, 45, avenue des Etats-Unis, 78035 Versailles Cedex, France.
authors.forename: Alexis
authors.initials: A
authors.lastname: Coste
authors.forename: Mathieu
authors.initials: M
authors.lastname: Toumi
authors.forename: Karen
authors.initials: K
authors.lastname: Wright
authors.forename: Vanessa
authors.initials: V
authors.lastname: Razafimahaléo
authors.forename: François
authors.initials: F
authors.lastname: Couty
authors.forename: Jérome
authors.initials: J
authors.lastname: Marrot
authors.forename: Gwilherm
authors.initials: G
authors.lastname: Evano
mesh_terms: D002384:Catalysis; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D004151:Dipeptides / Q000737:chemistry; D006847:Hydrocarbons, Iodinated / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis; D007211:Indoles / Q000138:chemical synthesis*; D011758:Pyrroles / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014364:Tryptophan / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D004151:Dipeptides; D006847:Hydrocarbons, Iodinated; D026121:Indole Alkaloids; D007211:Indoles; D011758:Pyrroles; D003300:Copper; D014364:Tryptophan