title: Formation of the Main Cores Present in Natural Products by Tandem Additions.
abstract: A rapid route to 5,5- and 5,6- bicyclic systems is provided by an 1,3-alkyl-shift process mediated by a hypervalent iodine reagent on aromatics. The structures obtained contain several unsaturations with different behaviors and reactivities. Such diversity allows further elaborations for the rapid formation of compact systems present in a variety of natural products. The potential for further transformations has been demonstrated by performing a double Michael addition. This cyclization process is regio- and stereoselective due to the presence of a former benzylic substituent. Furthermore, an extension of this approach has been accomplished on indole derivatives.
authors.affiliation: Département de chimie, Université du Québec à Montréal, Laboratoire de Méthodologie et Synthèse de Produits Naturels, C.P.8888, Succ. Centre-Ville, Montréal, H3C 3P8, Québec (Canada).
authors.forename: Kimiaka C
authors.initials: KC
authors.lastname: Guérard
authors.affiliation: Département de chimie, Université du Québec à Montréal, Laboratoire de Méthodologie et Synthèse de Produits Naturels, C.P.8888, Succ. Centre-Ville, Montréal, H3C 3P8, Québec (Canada).
authors.forename: Vincent
authors.initials: V
authors.lastname: Hamel
authors.affiliation: Département de chimie, Université du Québec à Montréal, Laboratoire de Méthodologie et Synthèse de Produits Naturels, C.P.8888, Succ. Centre-Ville, Montréal, H3C 3P8, Québec (Canada).
authors.forename: Amandine
authors.initials: A
authors.lastname: Guérinot
authors.affiliation: Département de chimie, Université du Québec à Montréal, Laboratoire de Méthodologie et Synthèse de Produits Naturels, C.P.8888, Succ. Centre-Ville, Montréal, H3C 3P8, Québec (Canada).
authors.forename: Cloé
authors.initials: C
authors.lastname: Bouchard-Aubin
authors.affiliation: Département de chimie, Université du Québec à Montréal, Laboratoire de Méthodologie et Synthèse de Produits Naturels, C.P.8888, Succ. Centre-Ville, Montréal, H3C 3P8, Québec (Canada). canesi.sylvain@uqam.ca.
authors.forename: Sylvain
authors.initials: S
authors.lastname: Canesi
mesh_terms: D001593:Benzyl Compounds / Q000737:chemistry*; D001688:Biological Products / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D003500:Cyclization; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D001593:Benzyl Compounds; D001688:Biological Products; D001643:Bridged Bicyclo Compounds; D007211:Indoles
keywords: alkyl shift; double Michael addition; hypervalent iodine; indoles; natural products