title: Mechanistic insights into the stereocontrolled synthesis of hexahydropyrrolo[2,3-b]indoles by electrophilic activation of tryptophan derivatives.
abstract: A three-step mechanism involving the formation and rearrangement of an intermediate with indoline-azetidine spirocyclic core structure was shown by DFT computations to account for the electrophilic cyclization of tryptophan derivatives to hexahydropyrrolo[2,3-b]indoles. The corresponding 3a-bromo derivatives have been obtained in high yields and synthetically useful exo/endo ratios.
authors: Departamento de Química OrgAnica, Universidade de Vigo, Lagoas-Marcosende, 36310 Vigo, Spain.
authors: Carlos Silva
authors: CS
authors: López
authors: Carlos
authors: C
authors: Pérez-Balado
authors: Paula
authors: P
authors: Rodríguez-Graña
authors: Angel R
authors: AR
authors: de Lera
mesh_terms: D003500:Cyclization; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014364:Tryptophan / Q000737:chemistry*
chemical_list: D006842:Hydrocarbons, Brominated; D007211:Indoles; D011758:Pyrroles; D014364:Tryptophan