A Formal [3 1 2] Alkene Addition to Benzhydrol Cations. A Practical and Mild Methodology for the Synthesis of Substituted 1-Arylindanes and Related Compounds

ABSTRACT We report the single step synthesis of several 1-arylindanes in good yield via a formal [3 þ 2] atom cycloaddition. cycloaddition relies on the Lewis acid activation of a bibenzylic alcohol in the presence of an alkene. The cation generated from the alcohol can be trapped by the alkene to afford a new benzylic cation which can then undergoes cyclization leading to 1-arylindanes with three stereogenic centres

Hydrogenation of (-)-menthone, (+)-isomenthone, and (+)-pulegone with platinum/tin catalysts

The hydrogenation of (-)-menthone, (+)-isomenthone, and (+)-pulegone over SiO2-supported Pt and Pt-Sn catalysts was studied in this work. The modification with tin was performed by means of the techniques of surface organometallic chemistry on metals. This way of modifying the catalysts allowed stereoisomers of menthol to be obtained in a one-step process. The hydrogenation of these terpenones was favored by the presence of tin in the bimetallic phase.Fil: Vetere, Virginia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; ArgentinaFil: Santori, Gerardo Fabian. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentina. Universidad Nacional de La Plata. Facultad de Ingeniería; ArgentinaFil: Moglioni, Albertina Gladys. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; ArgentinaFil: Moltrasio Iglesias, Graciela Y.. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica; ArgentinaFil: Casella, Mónica Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; ArgentinaFil: Ferretti, Osmar Alberto. Universidad Nacional de La Plata. Facultad de Ingeniería; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Investigación y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco". Universidad Nacional de la Plata. Facultad de Ciencias Exactas. Centro de Investigación y Desarrollo en Ciencias Aplicadas; Argentin

Reaction between N-alkylhydroxylamines and chiral enoate esters: More experimental evidence for a cycloaddition-like process, a rationale based on DFT theoretical calculations, and stereoselective synthesis of new enantiopure β-amino acids

The reactions between N-benzyl- and N-methylhydroxylamine and chiral enoate esters, derived from D-glyceraldehyde and (-)-verbenone, respectively, have been investigated. Theoretical calculations show that the most favorable mechanism involves the concerted cycloaddition of the hydroxylamine to the substrate. This result is in good agreement with the stereospecificity observed when the trisubstituted olefins are used. The open-chain adducts have been isolated when the processes are carried out at low temperatures and for short reaction times. These compounds evolve to the corresponding isoxazolidinones on standing at room temperature or under acid catalysis. The high π-facial diastereoselection has been rationalized on the basis of steric effects induced by the dioxolane ring for D-glyceraldehyde derivatives or by the cyclobutane gem-dimethyl substitution for esters prepared from (-)-verbenone. As an application of these reactions, new β-amino acids have been synthesized in a highly efficient and stereocontrolled manner.Fil: Moglioni, Albertina Gladys. Universitat Autònoma de Barcelona; España. Universidad de Buenos Aires; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Houssay; ArgentinaFil: Muray, Elena. Universitat Autònoma de Barcelona; EspañaFil: Castillo, José A.. Universitat Autònoma de Barcelona; EspañaFil: Álvarez Larena, Ángel. Universitat Autònoma de Barcelona; EspañaFil: Moltrasio, Graciela Y.. Universidad de Buenos Aires; ArgentinaFil: Branchadell, Vicenç. Universitat Autònoma de Barcelona; EspañaFil: Ortuño, Rosa M.. Universitat Autònoma de Barcelona; Españ

Synthesis of New Indanyl Nucleoside Analogues and their Biological Evaluation on Hepatitis C Virus (HCV) Replicon

Here, we report a convenient synthetic procedure for the preparation of four novel indanyl carbanucleoside derivatives in the racemic form. The action of these compounds against hepatitis C virus was evaluated in vitro using the replicon cell line, Huh7.5 SG. Contrary to our expectations, all these compounds did not inhibit, but rather promoted HCV genotype 1b (HCVg1b) replication. Similar effects have been reported for morphine in the replicon cell lines, Huh7 and Huh8. Several biological experiments and computational studies were performed to elucidate the effect of these compounds on HCVg1b replication. Based on all the experiments performed, we propose that the increase in HCVg1b replication could be mediated, at least in part, by a similar mechanism to that of morphine on the enhancement of this replication. The presence of opioid receptors in Huh7.5 SG cells was indirectly determined for the first time in this work