Literature DB >> 18844366

Stereocontrolled access to isoprostanes via a bicyclo[3.3.0]octene framework.

Camille Oger1, Yasmin Brinkmann, Samira Bouazzaoui, Thierry Durand, Jean-Marie Galano.   

Abstract

We report a simple and highly stereocontrolled strategy toward the total synthesis of isoprostanes based on a bicyclic alpha,beta-epoxy ketone intermediate 6. Bicyclo[3.3.0]octene scaffold permitted stereodirection of reagents allowing stereoselective epoxidation, diastereoselective ketone reduction, and regioselective epoxide opening otherwise not accessible with a simple cyclopentene framework.

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Year:  2008        PMID： 18844366     DOI： 10.1021/ol802104z

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  15 in total

Review 1.  Asymmetric Iridium-Catalyzed C-C Coupling of Chiral Diols via Site-Selective Redox-Triggered Carbonyl Addition.

Authors:  Inji Shin; Michael J Krische
Journal:  Top Curr Chem       Date:  2016

2.  F2-dihomo-isoprostanes as potential early biomarkers of lipid oxidative damage in Rett syndrome.

Authors:  Claudio De Felice; Cinzia Signorini; Thierry Durand; Camille Oger; Alexandre Guy; Valérie Bultel-Poncé; Jean-Marie Galano; Lucia Ciccoli; Silvia Leoncini; Maurizio D'Esposito; Stefania Filosa; Alessandra Pecorelli; Giuseppe Valacchi; Joussef Hayek
Journal:  J Lipid Res       Date:  2011-09-13       Impact factor: 5.922

3.  Diastereo- and Enantioselective Iridium Catalyzed Coupling of Vinyl Aziridines with Alcohols: Site-Selective Modification of Unprotected Diols and Synthesis of Substituted Piperidines.

Authors:  Gang Wang; Jana Franke; Chinh Q Ngo; Michael J Krische
Journal:  J Am Chem Soc       Date:  2015-06-15       Impact factor: 15.419

4.  Simultaneous quantitative profiling of 20 isoprostanoids from omega-3 and omega-6 polyunsaturated fatty acids by LC-MS/MS in various biological samples.

Authors:  Aude Dupuy; Pauline Le Faouder; Claire Vigor; Camille Oger; Jean-Marie Galano; Cédric Dray; Jetty Chung-Yung Lee; Philippe Valet; Cécile Gladine; Thierry Durand; Justine Bertrand-Michel
Journal:  Anal Chim Acta       Date:  2016-03-19       Impact factor: 6.558

5.  Catalyst-directed diastereo- and site-selectivity in successive nucleophilic and electrophilic allylations of chiral 1,3-diols: protecting-group-free synthesis of substituted pyrans.

Authors:  Inji Shin; Gang Wang; Michael J Krische
Journal:  Chemistry       Date:  2014-08-28       Impact factor: 5.236

6.  Protecting-group-free diastereoselective C-C coupling of 1,3-glycols and allyl acetate through site-selective primary alcohol dehydrogenation.

Authors:  Anne-Marie R Dechert-Schmitt; Daniel C Schmitt; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2013-01-31       Impact factor: 15.336

7.  Polymeric nanocapsules prevent oxidation of core-loaded molecules: evidence based on the effects of docosahexaenoic acid and neuroprostane on breast cancer cells proliferation.

Authors:  Jérôme Roy; Liliam Teixeira Oliveira; Camille Oger; Jean-Marie Galano; Valerie Bultel-Poncé; Sylvain Richard; Andrea Grabe Guimaraes; José Mário Carneiro Vilela; Margareth Spangler Andrade; Thierry Durand; Pierre Besson; Vanessa Carla Furtado Mosqueira; Jean-Yves Le Guennec
Journal:  J Exp Clin Cancer Res       Date:  2015-12-21

8.  Isoprostanoid Profiling of Marine Microalgae.

Authors:  Claire Vigor; Camille Oger; Guillaume Reversat; Amandine Rocher; Bingqing Zhou; Amandyne Linares-Maurizi; Alexandre Guy; Valérie Bultel-Poncé; Jean-Marie Galano; Joseph Vercauteren; Thierry Durand; Philippe Potin; Thierry Tonon; Catherine Leblanc
Journal:  Biomolecules       Date:  2020-07-18

Review 9.  Isoprostanes and 4-hydroxy-2-nonenal: markers or mediators of disease? Focus on Rett syndrome as a model of autism spectrum disorder.

Authors:  Cinzia Signorini; Claudio De Felice; Thierry Durand; Camille Oger; Jean-Marie Galano; Silvia Leoncini; Alessandra Pecorelli; Giuseppe Valacchi; Lucia Ciccoli; Joussef Hayek
Journal:  Oxid Med Cell Longev       Date:  2013-06-13       Impact factor: 6.543

10.  Lipid profiling following intake of the omega 3 fatty acid DHA identifies the peroxidized metabolites F4-neuroprostanes as the best predictors of atherosclerosis prevention.

Authors:  Cécile Gladine; John W Newman; Thierry Durand; Theresa L Pedersen; Jean-Marie Galano; Céline Demougeot; Olivier Berdeaux; Estelle Pujos-Guillot; Andrzej Mazur; Blandine Comte
Journal:  PLoS One       Date:  2014-02-18       Impact factor: 3.240
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