title: Seven-membered rings through metal-free rearrangement mediated by hypervalent iodine.
abstract: A versatile and metal-free approach for the synthesis of carbocycles and of heterocycles bearing seven- and eight-membered rings is described. The strategy is based on ring expansion of 1-vinylcycloalkanols (or the corresponding silyl or methyl ether) mediated by the hypervalent iodine reagent HTIB (PhI(OH)OTs). Reaction conditions can be easily adjusted to give ring expansion products bearing different functional groups. A route to medium-ring lactones was also developed.
authors.affiliation: Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, CP 26077, São Paulo-SP CEP 05513-970, Brazil. siguara.silva@usp.br.
authors.forename: Siguara Bastos Lemos
authors.initials: SB
authors.lastname: Silva
authors.affiliation: Division of Pharmacology and Toxicology, Multidisciplinary Center for Chemical, Biological and Agricultural, State University of Campinas, 6171, Campinas-SP CEP 13081-970, Brazil. adriana_biotec@yahoo.com.br.
authors.forename: Adriana Della
authors.initials: AD
authors.lastname: Torre
authors.affiliation: Division of Pharmacology and Toxicology, Multidisciplinary Center for Chemical, Biological and Agricultural, State University of Campinas, 6171, Campinas-SP CEP 13081-970, Brazil. carvalho_je@yahoo.com.br.
authors.forename: João Ernesto
authors.initials: JE
authors.lastname: de Carvalho
authors.affiliation: Division of Pharmacology and Toxicology, Multidisciplinary Center for Chemical, Biological and Agricultural, State University of Campinas, 6171, Campinas-SP CEP 13081-970, Brazil. analucia@cpqba.unicamp.br.
authors.forename: Ana Lúcia Tasca Gois
authors.initials: AL
authors.lastname: Ruiz
authors.affiliation: Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, CP 26077, São Paulo-SP CEP 05513-970, Brazil. luizfsjr@iq.usp.br.
authors.forename: Luiz F
authors.initials: LF
authors.lastname: Silva
mesh_terms: D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D006571:Heterocyclic Compounds / Q000737:chemistry* / Q000494:pharmacology; D006801:Humans; D007455:Iodine / Q000737:chemistry*; D008670:Metals / Q000737:chemistry*; D008958:Models, Molecular; D017646:Organosilicon Compounds / Q000737:chemistry
chemical_list: D006571:Heterocyclic Compounds; D008670:Metals; D017646:Organosilicon Compounds; D007455:Iodine; C024548:hexamethylsilazane