title: Direct oxidative coupling of N-acetyl indoles and phenols for the synthesis of benzofuroindolines related to phalarine.
abstract: Inspired by the biogenetic synthesis of benzofuroindoline-containing natural products, we designed an oxidative coupling between phenol and N-acetyl indoles. This straightforward and direct radical process, mediated by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and FeCl3 allowed the regioselective synthesis of benzofuro[3,2-b]indolines, whose structure is found in the natural product phalarine.
authors.affiliation: Univ. Paris Sud and CNRS, Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO), Equipe Méthodologie, Synthèse et Molécules Thérapeutiques, Bat. 410, 15 rue G. Clemenceau, 91405 Orsay (France) http://www.icmmo.u-psud.fr/Labos/LPSN/cv/guillaume.php.
authors.forename: Terry
authors.initials: T
authors.lastname: Tomakinian
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: D000470:Alkaloids / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D058451:Oxidative Coupling; D010636:Phenols / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D007211:Indoles; D010636:Phenols; C552076:phalarine
keywords: benzofuroindolines; indoles; oxidative coupling; phalarine; phenols