title: FeCl3-mediated Friedel-Crafts hydroarylation with electrophilic N-acetyl indoles for the synthesis of benzofuroindolines.
abstract: IRONic electrophilic indoles! The C3-regioselective hydroarylation of N-acetyl indoles with aromatic nucleophiles mediated by FeCl(3)  features a rare example of the electrophilic reactivity of the indole core in a Friedel-Crafts reaction. This indole umpolung allows us straightforward access to the tetracyclic benzofuroindoline motif found in the natural product diazonamide A, which is a potent antitumor agent.
authors.affiliation: Université Paris-Sud and CNRS, Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), UMR 8182, Laboratoire de Chimie des Procédés et Substances Naturelles, Bat. 410, 91405 Orsay, France.
authors.forename: Rodolphe
authors.initials: R
authors.lastname: Beaud
authors.forename: Régis
authors.initials: R
authors.lastname: Guillot
authors.forename: Cyrille
authors.initials: C
authors.lastname: Kouklovsky
authors.forename: Guillaume
authors.initials: G
authors.lastname: Vincent
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D005290:Ferric Compounds / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D010080:Oxazoles / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; D002712:Chlorides; D005290:Ferric Compounds; D006576:Heterocyclic Compounds, 4 or More Rings; D007211:Indoles; D010080:Oxazoles; C408862:diazonamide A; C057812:indoline; C030374:indole; C024555:ferric chloride