Copper-catalyzed cyclization of iodo-tryptophans: a straightforward synthesis of pyrroloindoles.
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.
Coste
Alexis
A
Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles Saint-Quentin en Yvelines, 45, avenue des Etats-Unis, 78035 Versailles Cedex, France.
Toumi
Mathieu
M
Wright
Karen
K
Razafimahaléo
Vanessa
V
Couty
François
F
Marrot
Jérome
J
Evano
Gwilherm
G
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
D004151:Dipeptides; D006847:Hydrocarbons, Iodinated; D026121:Indole Alkaloids; D007211:Indoles; D011758:Pyrroles; D003300:Copper; D014364:Tryptophan