Bruno Linclau

Summary

Affiliation: University of Southampton
Country: UK

Publications

  1. doi request reprint Investigating the Influence of (Deoxy)fluorination on the Lipophilicity of Non-UV-Active Fluorinated Alkanols and Carbohydrates by a New log P Determination Method
    Bruno Linclau
    Chemistry, University of Southampton, Highfield, Southampton, SO17 1BJ UK
    Angew Chem Int Ed Engl 55:674-8. 2016
  2. doi request reprint Intramolecular OH⋅⋅⋅Fluorine Hydrogen Bonding in Saturated, Acyclic Fluorohydrins: The γ-Fluoropropanol Motif
    Bruno Linclau
    Department of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ UK, Fax 44 23 8059 6805
    Chemistry 21:17808-16. 2015
  3. pmc An unexpected and significantly lower hydrogen-bond-donating capacity of fluorohydrins compared to nonfluorinated alcohols
    Jérôme Graton
    CEISAM UMR CNRS 6230, Faculte des Sciences et des Techniques, Universite de Nantes, 2, rue de la Houssinière BP 92208, 44322 Nantes Cedex 3, France
    Angew Chem Int Ed Engl 51:6176-80. 2012
  4. ncbi request reprint Stereoarrays with an all-carbon quaternary center: diastereoselective desymmetrization of prochiral malonaldehydes
    Bruno Linclau
    School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ UK
    Angew Chem Int Ed Engl 51:1232-5. 2012
  5. doi request reprint The conformation of tetrafluorinated methyl galactoside anomers: crystallographic and NMR studies
    Bruno Linclau
    School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, United Kingdom
    Carbohydr Res 346:1129-39. 2011
  6. doi request reprint Enantioselective synthesis of tetrafluorinated ribose and fructose
    Bruno Linclau
    School of Chemistry, University of Southampton, Highfield, Southampton, UK
    Org Biomol Chem 7:803-14. 2009
  7. ncbi request reprint Enantioselective synthesis and selective monofunctionalization of (4R,6R)-4,6- dihydroxy-2,8-dioxabicyclo[3.3.0]octane
    Bruno Linclau
    University of Southampton, School of Chemistry, Highfield, Southampton SO17 1BJ, U K
    Org Lett 8:5821-4. 2006
  8. doi request reprint Microwave-assisted ester formation using O-alkylisoureas: a convenient method for the synthesis of esters with inversion of configuration
    Alessandra Chighine
    School of Chemistry, University of Edinburgh, Joseph Black Building, West Mains Road, Edinburgh EH9 3JJ, United Kingdom
    J Org Chem 74:4753-62. 2009
  9. doi request reprint A linchpin carbacyclization approach for the synthesis of carbanucleosides
    Leo M H Leung
    School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK
    J Org Chem 73:9197-206. 2008
  10. ncbi request reprint A stereoselective cyclization to carbafuranose derivatives starting from 1,4-bis-epoxides
    Leo M H Leung
    School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, United Kingdom
    Org Lett 7:5183-6. 2005

Collaborators

  • Serge Van Calenbergh
  • Tim Elliott
  • Dirk Elewaut
  • Kylie Brown
  • Clement Q Fontenelle
  • A James Boydell
  • Leo M H Leung
  • Stefano Crosignani
  • Alex Weymouth-Wilson
  • Nathan Bartlett
  • Florent Larnaud
  • Zhong Wang
  • Mark Light
  • Jérôme Graton
  • Vincent Foucher
  • Alessandra Chighine
  • Roxana S Timofte
  • Leo Leung
  • Vicky Gibson
  • Mark Bradley
  • Patrick Lecarpentier
  • Florent Péron
  • Xavier Pannecoucke
  • Matthew D Selby
  • Matthew Conroy
  • Leona Gross
  • Daniel J Asby
  • Thomas Poisson
  • Michael Dixey
  • Ali Tavassoli
  • Emmanuel Pfund
  • Christine Fossey
  • Thomas Cailly
  • Julien Malassis
  • Frederic Fabis
  • Thierry Lequeux
  • Jean Yves Le Questel
  • Daniela Gonçalves Monteiro
  • Anne Marie Brossard
  • Marinus B Groen
  • Benedetta Guizzardi
  • Marie Claire Arnal
  • Tine Decruy
  • Aymen Al-Shamkhani
  • Katrien Van Beneden
  • Christian Ottensmeier
  • Joern Werner
  • Cyrille Tomassi
  • Tony Williams
  • Mark E Light
  • Victoria Vinader
  • Eva Bürkstümmer
  • Martin J Jeffery
  • Delphine Launay

Detail Information

Publications24

  1. doi request reprint Investigating the Influence of (Deoxy)fluorination on the Lipophilicity of Non-UV-Active Fluorinated Alkanols and Carbohydrates by a New log P Determination Method
    Bruno Linclau
    Chemistry, University of Southampton, Highfield, Southampton, SO17 1BJ UK
    Angew Chem Int Ed Engl 55:674-8. 2016
    ..Interesting trends and changes, for example, for the dependence on relative stereochemistry, are reported. ..
  2. doi request reprint Intramolecular OH⋅⋅⋅Fluorine Hydrogen Bonding in Saturated, Acyclic Fluorohydrins: The γ-Fluoropropanol Motif
    Bruno Linclau
    Department of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ UK, Fax 44 23 8059 6805
    Chemistry 21:17808-16. 2015
    ..These results provide new insights of the impact of fluorination of aliphatic alcohols, with attractive perspectives for rational drug design. ..
  3. pmc An unexpected and significantly lower hydrogen-bond-donating capacity of fluorohydrins compared to nonfluorinated alcohols
    Jérôme Graton
    CEISAM UMR CNRS 6230, Faculte des Sciences et des Techniques, Universite de Nantes, 2, rue de la Houssinière BP 92208, 44322 Nantes Cedex 3, France
    Angew Chem Int Ed Engl 51:6176-80. 2012
  4. ncbi request reprint Stereoarrays with an all-carbon quaternary center: diastereoselective desymmetrization of prochiral malonaldehydes
    Bruno Linclau
    School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ UK
    Angew Chem Int Ed Engl 51:1232-5. 2012
    ..In the same pot, addition of a second nucleophile proceeds in high diastereoselectivity to generate nonsymmetric products with up to five contiguous stereogenic centers, including a chiral all-carbon quaternary center...
  5. doi request reprint The conformation of tetrafluorinated methyl galactoside anomers: crystallographic and NMR studies
    Bruno Linclau
    School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, United Kingdom
    Carbohydr Res 346:1129-39. 2011
    ..There is one close OH⋯F contact, which is likely to arise from the crystal packing. NMR studies show that the two anomers also adopt a (4)C(1) conformation in solution (D(2)O, CDCl(3))...
  6. doi request reprint Enantioselective synthesis of tetrafluorinated ribose and fructose
    Bruno Linclau
    School of Chemistry, University of Southampton, Highfield, Southampton, UK
    Org Biomol Chem 7:803-14. 2009
    ..A perfluoroalkylidene lithium mediated cyclisation approach for the enantioselective synthesis of a tetrafluorinated aldose (ribose) and of a tetrafluorinated ketose (fructose), both in the furanose and in the pyranose form, is described...
  7. ncbi request reprint Enantioselective synthesis and selective monofunctionalization of (4R,6R)-4,6- dihydroxy-2,8-dioxabicyclo[3.3.0]octane
    Bruno Linclau
    University of Southampton, School of Chemistry, Highfield, Southampton SO17 1BJ, U K
    Org Lett 8:5821-4. 2006
    ..An efficient, enantioselective synthesis of a disubstituted bis-THF scaffold 5 is described, as well as an efficient differentiation of the 1,3-diol unit. [reaction: see text]..
  8. doi request reprint Microwave-assisted ester formation using O-alkylisoureas: a convenient method for the synthesis of esters with inversion of configuration
    Alessandra Chighine
    School of Chemistry, University of Edinburgh, Joseph Black Building, West Mains Road, Edinburgh EH9 3JJ, United Kingdom
    J Org Chem 74:4753-62. 2009
    ....
  9. doi request reprint A linchpin carbacyclization approach for the synthesis of carbanucleosides
    Leo M H Leung
    School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK
    J Org Chem 73:9197-206. 2008
    ..Both methods relied on Mitsunobu chemistry, and the first example of the Mukaiyama modification of the Mitsunobu reaction involving nucleobases as nucleophiles is reported...
  10. ncbi request reprint A stereoselective cyclization to carbafuranose derivatives starting from 1,4-bis-epoxides
    Leo M H Leung
    School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, United Kingdom
    Org Lett 7:5183-6. 2005
    ....
  11. doi request reprint Ready synthetic access to enantiopure allylic α(F)-branched fluoroalkenes
    Florent Larnaud
    Laboratoire de Chimie Moleculaire et Thioorganique, UMR CNRS 6507 and FR3038, ENSICAEN, Universite de Caen Basse Normandie, 6 boulevard du Marechal Juin, 14050 Caen, France, and Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, U K
    Org Lett 15:2450-3. 2013
    ..Convenient access to homochiral fluoroalkenes is described via a Julia-Kocienski olefination reaction. The required homochiral fluorosulfone is synthesized by a Mitsunobu reaction from readily available enantiopure secondary alcohols. ..
  12. doi request reprint A novel, versatile D-->BCD steroid construction strategy, illustrated by the enantioselective total synthesis of estrone
    Vincent Foucher
    University of Southampton, School of Chemistry, Highfield, Southampton SO17 1BJ, United Kingdom
    Org Lett 12:680-3. 2010
    ..The method is illustrated by the total synthesis of estrone via a C-ring closing metathesis and a B-ring Heck cyclization...
  13. ncbi request reprint Enantioselective synthesis of tetrafluoroethylene-containing monosaccharides
    A James Boydell
    Department of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK
    Angew Chem Int Ed Engl 43:5677-9. 2004
  14. ncbi request reprint A practical synthesis of a high-loading solid-supported IBX amide for the oxidation of alcohols
    Patrick Lecarpentier
    Combinatorial Centre of Excellence, School of Chemistry, University of Southampton, Highfield, Southampton, SO17 1BJ, UK
    Mol Divers 9:341-51. 2005
    ..Oxidation of a range of alcohols to the corresponding carbonyl compounds proved very straightforward using 1.2 equiv of the resin. Recycling of the resin was also possible with minimal loss of activity after two reoxidations...
  15. doi request reprint Enantioselective synthesis of tetrafluorinated glucose and galactose
    Roxana S Timofte
    University of Southampton, School of Chemistry, Highfield, Southampton SO17 1BJ
    Org Lett 10:3673-6. 2008
    ....
  16. ncbi request reprint Stereoselectivity of the Honda-Reformatsky Reaction in Reactions with Ethyl Bromodifluoroacetate with α-Oxygenated Sulfinylimines
    Clement Q Fontenelle
    Department of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, United Kingdom
    J Org Chem 79:4186-95. 2014
    ..Excellent diastereoselectivities (>94:6) are obtained for the matched cases. In contrast, reaction with sulfinylimines derived from unsubstituted alkanals proceeded with virtually no diastereoselectivity. ..
  17. doi request reprint A linear synthesis of gemcitabine
    Kylie Brown
    Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK Dextra Laboratories Ltd, The Science and Technology Centre, Earley Gate, Whiteknights Road, Reading RG6 6BZ, UK
    Carbohydr Res 406:71-5. 2015
    ..The process proceeded with modest anomeric selectivity. ..
  18. doi request reprint Design of fluorinated 5-HT(4)R antagonists: influence of the basicity and lipophilicity toward the 5-HT(4)R binding affinities
    Clement Q Fontenelle
    Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK
    Bioorg Med Chem 21:7529-38. 2013
    ..3,3,3-Trifluoropropyl and 4,4,4-trifluorobutyl derivatives 6d and 6e have shown to bind to the 5-HT(4)R while maintaining their pharmacological profile and selectivity toward other 5-HT receptors...
  19. ncbi request reprint Short synthesis of enantiopure C2-symmetric 1,2:4,5-diepoxypentane and "pseudo"-C2-symmetric 3-azido-1,2:4,5-diepoxypentane from arabitol
    A James Boydell
    Department of Chemistry, Southampton University, Highfield, Southampton SO17 1BJ, UK
    J Org Chem 68:8252-5. 2003
    ..Both enantiomers of 1 and 4 are accessible, and all reactions involved are easily amenable for large-scale synthesis...
  20. doi request reprint Stereocontrol by quaternary centres: a stereoselective synthesis of (-)-luminacin D
    Nathan Bartlett
    Department of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ UK
    Chemistry 20:3306-10. 2014
    ..This reaction was used as a key step in an enantioselective synthesis of the angiogenesis inhibitor luminacin D. ..
  21. doi request reprint The synthesis of gemcitabine
    Kylie Brown
    Department of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK Dextra Laboratories Ltd, The Science and Technology Centre, Earley Gate, Whiteknights Road, Reading RG6 6BZ, UK
    Carbohydr Res 387:59-73. 2014
    ....
  22. doi request reprint Synthesis and in vivo evaluation of 4-deoxy-4,4-difluoro-KRN7000
    Leo Leung
    School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK
    Org Lett 10:4433-6. 2008
    ..The biological evaluation reveals a bias toward Th1 cytokine induction upon Natural Killer T cell activation...
  23. ncbi request reprint Microwaves, supported-reagents and parallel synthesis: isocyanide and ester synthesis
    Stefano Crosignani
    Combinatorial Centre of Excellence, Department of Chemistry, University of Southampton, Highfield, Southampton, UK
    Mol Divers 7:203-10. 2003
    ..Not only were reaction times dramatically reduced but the transformations were less prone to side reactions and decomposition...
  24. pmc Synthesis and crystallographic analysis of meso-2,3-difluoro-1,4-butanediol and meso-1,4-dibenzyloxy-2,3-difluorobutane
    Bruno Linclau
    School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, UK
    Beilstein J Org Chem 6:62. 2010
    ..Monosilylation of the diol is high-yielding but all attempts to achieve chain extension through addition of alkyl Grignard and acetylide nucleophiles failed...