Programme & Book of Abstracts

438
Journées de Chimie Organique JCO 2016 7 > 9 September 2016 Ecole Polytechnique Palaiseau, France Programme & Book of Abstracts

Transcript of Programme & Book of Abstracts

  • Journes de Chimie

    Organique

    JCO 20167 > 9 September 2016Ecole Polytechnique

    Palaiseau, France

    Programme & Book of Abstracts

  • Programme & Book of Abstracts

    JCO 20167 > 9 September 2016Ecole Polytechnique

    Palaiseau, France

    Journes de Chimie

    Organique

  • 2

    JCO 2016

    ContentOrganising Committee ........................................................................................................2

    Welcome ..............................................................................................................................3

    Sponsors - Partner ...............................................................................................................4

    Exhibitors .............................................................................................................................5

    Programme at a glance ........................................................................................................6

    Programme ..........................................................................................................................7

    Invited lectures and Biographies ........................................................................................13

    Oral communications .........................................................................................................49

    Posters .............................................................................................................................113

    Index of authors ...............................................................................................................415

    List of attendees ...............................................................................................................425

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  • 13

    JCO 2016

    Invited lectures and Biographies

  • 14

    invited lecture >> JCO 2016

    Vronique GOUVERNEURProfessor of Chemistry - University of OxfordBorn November 8, 1964 in Geel (Belgium); Chemistry Research Laboratory; 12 Mansfield Road- Oxford - OX1 3TA (UK)Phone & Fax: 44 (1865) 275 644 E-mail: [email protected] group web site: http://research.chem.ox.ac.uk/veronique-gouverneur.aspx

    EMPLOYMENT and EDUCATION2008- Professor of Chemistry, Oxford University, Department of Chemistry; Tutorial Fellowship (TF), Merton College (UK)2006-2008 Reader in Organic Chemistry, Oxford University, Department of Chemistry; TF Merton College (UK)1998-2006 University Lecturer in Organic Chemistry, Oxford University, Department of Chemistry; TF Merton College (UK)1994-1998 Matre de Confrences & Associate Member of ISIS; Universit Louis Pasteur Strasbourg (France)1992-1994 Postdoctoral Research Fellow Mentor: Prof. R. A. Lerner The Scripps Research Institute, La Jolla CA (USA)1985-1991 Ph.D. (la Plus Grande Distinction) Mentor: Prof. L. Ghosez; Universit Catholique de Louvain, LLN (Belgium)1981-1985 B.Sc and M.Sc in Chemistry (la Plus Grande Distinction); Universit Catholique de Louvain, LLN (Belgium)

    AWARDS, HONOURS, ESTEEM INTERNATIONAL RECOGNITIONAwards & Prizes: 2016 Tetrahedron Chair BOSS XV; 2015 ACS Award for Creative Work in Fluorine Chemistry; 2013-2018 Royal Society Wolfson Research Merit Award; 2012, Chaire Internationale de Recherche Blaise Pascal (ENS/CEA-France); 2011, Distinguished Woman in Chemistry or Chemical Engineering Award - ACS Challenge Year of Chemistry Celebration; 2011, Liebig Lectureship Award of the Organic Division of the German Chemical Society; 2010, The Thieme Chemistry Journal Award; 2008, The RSC Bader Award; 2005, The AstraZeneca Research Award in Organic Chemistry; 2000, The Nuffield Foundation Award for Newly Appointed University Lecturer; 1992, Prix de lAcadmie Royale des Sciences Belgium; 1992 Prix Bruylants. Esteem International Recognitions: 2018, Chair (co-chairs: Prof D. OHagan and Prof G. Sandford) of the International Symposium on Fluorine Chemistry; 2016-, Chair Chem. Commun. (RSC); 2015-2018, President of EuCheMS Organic Division; 2015-, Editorial Board Beilstein J. Org. Chemistry; 2014-, Member of the International Scientific Advisory Board of ENSCP (France); 2013 Clayton H. Heathcock Lectureship in Organic Chemistry, Berkeley (USA); 2011-2013, Executive Committee Member of ACS Fluorine Division (USA); 2011-, Chemistry sub-programme Director - Oxford Cancer Imaging Centre; 2011-, Member of the Academic Advisory Board Advanced Synthesis and Catalysis; 2010, Visiting Professor Shanghai Institute of Organic Chemistry (China); 2010, Invited Professor - CDP Innovation Fabulous Fluorine (France); 2010, Visiting Professor University of Paris X (France); 2009-, Member of the Imaging Management Board University of Oxford (FMRIB); 2009, Vice-President RSC Organic Division; 2009, Member of the Royal Society Organic Chemistry Awards Committee; 2009, Member of the Moissan Prize Committee (French Chemical Society); 2007-2012, Member of the Editorial Board of Organic and Biomolecular Chemistry; 2007-, UK representative of EuCheMS Organic Division; 2007-2011, Chairman of the RSC Fluorine Subject Group; 2006-, Member of the EPSRC Peer Review College.

    PUBLICATIONS, PATENTS and BOOKS: 162 Publications in Peer Reviewed Journals (recent papers published in Chem. Commun., Chem. Sci., ACIE, JACS and Nature Chemistry); 9 Patents; 10 Book Chapters; Editor 1 Book (Editor).5. 18F-Labeling of Aryl-SCF3, -OCF3 and OCHF2 with [18F]Fluoride, T. Khotavivattana, S. Verhoog, M. Tredwell, L. Pfeifer, S. Calderwood, K. Wheelshouse, T. L. Collier, V. Gouverneur Angew. Chem. Int. Ed. 2015, 54, 9991-9995. 4. A General Copper-Mediated Nucleophilic 18F Fluorination of Arenes, M. Tredwell, S. M. Preshlock, N. J. Taylor, S. Gruber, M. Huiban, J. Passchier, J. Mercier, C. Gnicot, V. Gouverneur Angew. Chem. Int. Ed. 2014, 53, 7751-7755. Highlighted in Chemical and Engineering News and Synfacts. 3. A Broadly Applicable [18F]Trifluoromethylation of Aryl and Heteroaryl Iodides for PET Imaging, M. Huiban, M. Tredwell, S. Mizuta, Z. Wan, X. Zhang, T. Lee Collier, V. Gouverneur,* J. Passchier* Nature Chemistry 2013 5, 941-944; highlighted in Science Expanding the scope of fluorine tags for PET imaging by H.F. Kung et al. Science 10/2013; 342(6157):429-30; 2. Catalytic Hydrotrifluoromethylation of Unactivated Alkenes, S. Mizuta, S. Verhoog, K.M. Engle, T. Khotavivattana M. ODuill, K. Wheelhouse, G. Rassias, M. Medebielle, V. Gouverneur* J. Am. Chem. Soc. 2013 135(7), 25052508. Highlighted in Chemical and Engineering News; 1. Organocatalyzed Enantioselective Fluorocyclization, O. Lozano, G. Blessley, T.M. del Campo, A.L. Thompson, G.T. Giuffredi, M. Bettati, M. Walker, R. Borman, V. Gouverneur* Angew. Chem. Int. Ed. 2011, 50, 81058109.

    SUPERVISION: 38 Postdoctoral Research Fellows; 35 D Phil Thesis awarded and 10 D Phil Thesis ongoing; 54 Master Thesis awarded and 1 ongoing; 12 Visiting Students (Erasmus). Current number of group members: 24.

    FUNDING PORTFOLIO: Total number of Grants: 58; Total Value: 18 M inclusive of infrastructure grants (radiochemistry laboratory - Oxford chemistry); Total Value as Principal Investigator: 9.5 M, this includes PI/Coordinator of FP7-PEOPLE- 2012-ITN RADIOMI - Innovative Radiochemistry to Advance Molecular Imaging (http://radiomi.chem.ox.ac.uk/, Euros 3.9 M); Funding Bodies: EPSRC, BBSRC, MRC, EU (FP6 and FP7), Leverhulme Trust, Royal Society, Royal Society of Chemistry, Cancer Research UK; Eli Lilly, UCB; Rhodia; Pfizer; GSK; AstraZeneca; Syngenta; Hammersmith Imanet [GE Healthcare]; Siemens Molecular Imaging; Department of Trade and Industry.

    118 Plenary/Keynote lectures at INTERNATIONAL CONFERENCES and 116 RESEARCH LECTURES (academia, industry)

  • 15

    invited lecture >> JCO 2016 IL 01

    FLUORINE CHEMISTRY CUSTOMIZED FOR DRUG DISCOVERY

    Vronique GOUVERNEUR

    1University of Oxford, Chemistry Research laboratory12 Mansfield Road, OX1 3TA, Oxford (UK)

    [email protected]

    The impact of fluorine chemistry in the life sciences is enormous. As many as 3040% of agrochemicals and 20% of pharmaceuticals on the market are estimated to contain fluorine. 18F-labeled compounds are also critically important for Positron Emission Tomography [PET]. As a result, there is an increasing demand for facile methods allowing for the fluorination of a large variety of structurally complex and functionalized targets using either 19F-reagents or the cyclotron produced radioisotope 18F. This lecture will discuss our recent contributions to late stage fluorination and 18F-radiochemistry; new methods expanding radiochemical space available for PET imaging will be presented as well as our approach to bridge the gap between fundamental research in radiochemistry, drug discovery and clinical applications.

  • 16

    invited lecture >> JCO 2016

    Marie-Paule TEULADE-FICHOU

    Dr. Marie-Paule Teulade-Fichou is a Research Director (1st Class) at CNRS. She was originally educated in Biochemistry and Pharmacology at University Denis Diderot (ParisVII) working on analogues of Platelet Activating Factor (3eme cycle doctorate in Pharmaceutical Chemistry in 1984 under the guidance of Prof. Jean-Jacques Godefroid) and then graduated in Chemistry at the University Pierre & Marie Curie (Paris VI) working on new methodology for phosphorus-carbon bond formation (PhD Doctorate in Organic Chemistry in 1986 under the guidance of Dr. P. Savignac).

    She then took up a position at CNRS in 1986, to develop research on organophosphorus compounds in the labora-tory of Phosphorus Chemistry headed by Prof. Franois Mathey at the Ecole Polytechnique.

    In 1991 she joined the group of Prof. Jean-Marie Lehn in Paris (Laboratory of Chemistry of Molecular Interactions, College de France) where she developed macrocylic chemistry for recognition of nucleic acids. In parallel she started targeting higher order DNA helices with small molecules in close collaboration with the group of Prof. Claude Hlne and in particular the team of Dr. Jean-Louis Mergny.

    In 2007 she moved to the Institute Curie where she was subsequently deputy director and director of the Chemistry research unit (CNRS-UMR176).

    Since January 2015 she is head of the newly created research unit Chemistry, Modelling and Imaging for Biology (CNRS-UMR9187 / INSERM-U1196). Dr. M.-P. Teulade-Fichou is team-leader of the group Structure and Fluores-cence Probes for Nucleic Acids, she has published > 150 articles in the field of organic chemistry and bioorganic chemistry of nucleic acids and she is co-inventor of 5 patents). In 2015 she has been awarded the silver medal of the CNRS-institute of chemistry.

    Research topics:

    Our current interest is focused on the design of new nucleic acids targeted compounds for anticancer research and for elucidating DNA-related molecular basis of cancer. In detail our work is focused on targeting unusual secondary DNA (and RNA) structures found in repeat sequences such as quadruplexes, hairpins and mismatches.

    The primary objective of this research is to provide structure probes usable in cells for exploring the polymorphism and dynamics of DNA and for studying recognition by proteins such as helicases, repair proteins and telomeric cha-perones. The development of DNA-targeted light-up probes represents a subtopic of our research.

    Over the past 15 years the design of selective quadruplex DNA-interactive compounds has constituted a central research topic of the group (> 60 articles). This has led to the development of several original chemical series and in particular to the identification of the phenanthroline derivative PhenDC3 currently used as quadruplex benchmark probe worldwide.

    Ultimately, we aim at the discovery of better targeted regiospecific DNA interactive compounds that may become new anticancer therapeutic agents.

  • 17

    invited lecture >> JCO 2016 IL 02

    CHEMISTRY IN ACTION ON DNA: MOLECULAR TOOLS FOR TARGETING AND IMAGING NUCLEIC

    ACID STRUCTURES

    Marie-Paule TEULADE-FICHOU

    Institut Curie, Research unit Chemistry Modelling and Imaging for Biology (CMIB), CNRS UMR 9187-INSERM U1196, Universit Paris-Sud 91405 Orsay, France.

    [email protected] ; http// cmib.curie.fr

    For many years our research efforts have been focused on the design of structure and fluorescence probes for targeting and imaging nucleic acids. Our targets are more specifically alternative secondary structures such as G-quadruplexes that can be found in G-rich regions as well as local pairing defects such as base mismatches that result from base misincorporation or chemical damages. These alternative structures are involved in various genomic dysfunctions and may ultimately cause genetic instability related to cancer development. Our aim is to provide chemical biology tools for better understanding the roles of these structures and their processing by proteins. In parallel targeted probes may enable identification of prototype scaffolds for anticancer drug development. Along these lines, we have developed a number of new heterocyclic scaffolds that have been engineered to display on the one hand selective recognition of the target DNA structure and on the other hand a switchable fluorescence emission acting as reporter. Selected examples illustrating our main achievements in the field will be described: 1) Design of bisquinolinium scaffolds acting as G-quadruplex DNA probes [1,5] 2) Design of Cyclobismacrocycles binding to homopyrimidine mismatches [6,8] 3) Design of Vinyl-Triphenylamine dyes shaped for two-photon absorption and AT-rich regiospecificity..[9,11] In each case, we will give a short overview of the synthetic approaches, the structure of the interaction with DNA identified by NMR or modelling and the practical applications for in vitro analysis and in-cell probing.

    References: [1] De Cian et al Highly efficient Bisquinolinum compounds for quadruplex recognition J.Amer. Chem.Soc. 2007, 129, 1856-1857. [2]P. Yang et al. Engineering Bisquinolinium-Thiazole orange conjugates for fluorescent sensing of G-quadruplex DNA Angew.Chem.Int Ed. 2009,48, 2188-2191. [3] E.Largy et al. Visualizing quadruplexes: from fluorescent ligands to light up probes Topics in Current Chem. 2013, Vol 330, 111177. [4] D. Verga et al. Photocrosslinking Probes for Trapping G-Quadruplex DNA Angew.Chem.Int.Ed. 2014, 53, 994-998. [5] A.Piazza et al. Short loop-length and high thermal stability determine genomic instability induced by G-quadruplex-forming minisatellites EMBO J. 2015, Volume 34, Issue 12, 1718-173. [6] A.Granzhan, N.Kotera, M.-P. Teulade-Fichou. Finding Needles in a Basestack: Recognition of Mismatched Base Pairs in DNA by Small Molecules Chem. Soc. Rev., 2014, 43, 3630-3665. [7] A.Granzhan, M.-P. Teulade-Fichou A Fluorescent Bisanthracene Macrocycle discriminates between matched and mismatch-containing DNA. Chemistry Eur.J. 2009, 15, 1314-1318. [8 M. Jourdan,et al. Double threading at DNA: NMR structure of a TT MM by a Bisnaphthalene macrocycle. Nucleic Acids Res. 2012 , 40, 5115-5128.[9] G. Bordeau et al. Trinaphthylamines as robust organic material for two-photon-induced fluorescence J.Am.Chem. Soc.2008, 130,16836-16837. WO2008/055969. [10] B.Dumat et al. DNA switches on the two-photon efficiency of an ultrabright triphenylamine dye with exquisite AT regiospecificity. J.Am.Chem. Soc.2013, 135, 12697-12706. [11] R. Chennoufi et al. Mitochondria-targeted Triphenylamine Derivatives Activatable by Two-Photon Excitation for Triggering and Imaging Cell Apoptosis Scientific Reports 2016 , 6(21458), 1-12.

  • 18

    invited lecture >> JCO 2016

    Amlie MARTINDocteur en chimie organique

    Formation

    2012 - 2015 Doctorat de chimie organique Institut de Chimie des milieux et matriaux de Poitiers (IC2MP) Utilisation des conditions superacides pour la mise en vidence dintermdiaires ractionnels glycosidiques (ANR Oxycarb) Publication: A. Martin et al., Nat. Chem., 2016, 8(2), 186-191. Communications: CFCF (Mai 2014 Gif s/ Yvette), SECO51 (Mai 2014 Port Leucate) Organisation de congrs : SECO52 (Mai 2015 Morzine) et Glycosyl Cation Day (Dcembre 2015 Poitiers)2009 - 2012 Diplme dingnieur Ecole Nationale Suprieure de Chimie de Mulhouse (ENSCMu) option chimie organique et bioorganique Master 2 Recherche Universit de Haute-Alsace option synthse organique2006 - 2009 Classes Prparatoires aux Grandes Ecoles Lyce Assomption, Rennes2006 Baccalaurat scientifique Lyce Priv dAvesnires, Laval mention Bien

    Expriences

    Sept 2013 Sept 2015 Universit de Poitiers Doctorant Contractuel Activit Complmentaire dEnseignement TD/TP enseigns en licence 1re, 2e et 3e anneJanvier 2015 CICBiogune (Bilbao Espagne) Doctorant Modlisation molculaireFvrier 2012 Sept 2012 SANOFI (Chilly-Mazarin) Stagiaire ingnieur Dveloppement de molcules potentiellement activesJuillet 2011 Aot 2009 FuturaFinances (Loiron) Opratrice Etiquetage, manutentionAvril 2011 Juin 2011 Universit de Haute-Alsace (Mulhouse) Stagiaire recherche Dveloppement de molcules thrapeutiquesJuillet 2010 Mann-Hummel (Laval) Stagiaire technicien Analyses microscopiques de soudures plastiques

  • 19

    invited lecture >> JCO 2016 IL 03

    USE OF SUPERACID CONDITIONS TO HIGHLIGHT UNPRECEDENTED TRANSIENT INTERMEDIATES IN

    GLYCOCHEMISTRY

    Amlie MARTIN,1 Ana ARDA,2 Jrme DESIRE,1 Agns MINGOT,1 Jess JIMENEZ-BARBERO,2 Sbastien THIBAUDEAU,1 Yves BLERIOT,1

    1Universit de Poitiers, UMR-CNRS 7285, IC2MP, Equipe Synthse organique, 4 rue Michel Brunet, TSA 51106,

    Poitiers Cedex 9 86073, France. 2CIC bioGUNE, Parque Tecnolgico de Bizkaia, Edif. 801A-1, Derio-Bizkaia 48160, Spain.

    [email protected], http://glyco.labo.univ-poitiers.fr/ A vast majority of biologically and therapeutically active carbohydrates exist as glycans (polysaccharides or complex glycoconjugates) in which monosaccharide units are joined via the glycosylation reaction. But surprisingly the details of the glycosidic bond formation remain relatively poorly understood.[1] Thus, highlighting this ion is a challenging task that could be useful to rationalize the stereochemical outcome of glycosylation reactions. Furthermore, the data associated with this ion could be exploited to improve the synthesis of oligosaccharides and glycoconjugates. Several research groups mainly based in the US[2] and Japan[3] are involved in the quest for the oxycarbenium ion using various approaches. In addition, the exceedingly short life of non-stabilized glycosyl cations in organic solution makes their delicate direct observation. The aim of the project is based on the use two chemistries: glycochemistry and superacid[4] and two analytical techniques by low-temperature NMR assisted by computational study to generate, identify and fully characterize the glycosyl cations. After generating transient species in superacid media, the long-lived intermediates as the known dioxalenium and oxazolinium ions are studied by in situ NMR. From peracetylated 2-deoxy and 2-bromoglucopyranose, the glycosyl cation is generated and deeply analysed for the first time in a condensed phase. NMR aided by complementary computations predicts the privileged three-dimensional structural for each intermediate. The trapping by even poor nucleophile further confirms the impact of the structure of the glycosyl cation on the stereochemical outcome.[5]

    References: [1] National Research Council, Transforming Glycoscience: A Roadmap for the Future, National Academies Press, 2012. [2] D. Crich, Acc. Chem. Res., 2010, 43, 1144-1153; D. M. Smith, K.A. Woerpel, Org. Biomol. Chem., 2006, 7, 1195-1201. [3] K. Matsumoto, K. Ueoka, S. Suzuki, S. Suga, J-I. Yoshida, Tetrahedron, 2009, 65, 10901-10907. [4] G. K. Olah, G. K. Surya Prakash, A. Molnr, J. Sommer, Superacid Chemistry, John Wiley & Sons, New Jersey, 2009. [5] A. Martin, A. Arda, J. Dsir, A. Martin-Mingot, N. Probst, P. Sina, J. Jimnez-Barbero, S. Thibaudeau, Y. Blriot, Nat. Chem., 2016, 8, 186-191.

  • 20

    invited lecture >> JCO 2016

    David LEIGHBorn 31 May 1963, Birmingham, EnglandNationality: BritishEmail: [email protected] website www.catenane.net OrchidID orcid.org/0000-0002-1202-4507 ResearcherID K-5965-2015Address School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, UK

    Academic Career 2014- Sir Samuel Hall Chair of Chemistry, School of Chemistry, University of Manchester, UK.2012-2013 Professor of Organic Chemistry, School of Chemistry, University of Manchester, UK.2001-2012 Forbes Chair of Organic Chemistry, School of Chemistry, University of Edinburgh, UK1998-2001 Chair of Synthetic Chemistry, Department of Chemistry, University of Warwick, UK1989-1998 Lectureship in Organic Chemistry, Department of Chemistry, University of Manchester Institute of Science and Technology, Manchester, UK 1987-1989 Postdoctoral Fellow at the National Research Council of Canada, Biological Sciences Division, Ottawa, Canada. 1984-1987 PhD, University of Sheffield, UK 1981-1984 BSc Special Honours in Chemistry, University of Sheffield, UK

    Awards & Prizes2003 Royal Society of Chemistry Award for Supramolecular Chemistry2004 Royal Society of Chemistry Award for Interdisciplinary Research2005 Institute of Chemistry of Ireland Award for Chemistry2005 Swiss Chemical Society Troisime Conferencier in Chemistry2005-10 EPSRC Senior Research Fellowship2005-10 Royal Society-Wolfson Research Merit Award2005 Elected Fellow of the Royal Society of Edinburgh, Scotlands National Academy of Science & Letters2005 Royal Society of Chemistry Award for Nanotechnology2007 International Izatt-Christensen Award for Macrocyclic Chemistry2007 Royal Society of Chemistry-Real Sociedad Espaola de Qumica (RSC-RSEQ) Prize for Chemistry2007 Feynman Prize for Nanotechnology2007 EU Descartes Prize for Research2008 ERC Advanced Grant (inaugural call) 2009 Royal Society of Chemistry Merck Award for Organic Chemistry2009 Elected Fellow of the Royal Society (London)2010 Royal Society of Chemistry Tilden Prize2013 Royal Society Bakerian Prize Lecture & Medal2013 ERC Advanced Grant 2014 Royal Society of Chemistry Pedler Award2015 Elected to the Academia Europaea, the European Academy of Science, Humanities & Letters

    H-index: 66 (GooSch, 22 April 2016); Citations: 16,617 (GooSch, 22 April 2016).

  • 21

    invited lecture >> JCO 2016 IL 04

    MAKING THE TINIEST MACHINES

    David A. LEIGH,1

    1 School of Chemistry, University of Manchester, Manchester, United Kingdom [email protected], www.catenane.net

    Over the past few years some of the first examples of synthetic molecular level machines and motorsall be they primitive by biological standardshave been developed.[1] Perhaps the best way to appreciate the technological potential of controlled molecular-level motion is to recognize that nanomotors and molecular-level machines lie at the heart of every significant biological process. Over billions of years of evolution Nature has not repeatedly chosen this solution for achieving complex task performance without good reason. When we learn how to build artificial structures that can control and exploit molecular level motion, and interface their effects directly with other molecular-level substructures and the outside world, it will potentially impact on every aspect of functional molecule and materials design.[2-5]

    References [1] E. R. Kay, D. A. Leigh, Angew. Chem. Int. Ed. 2015, 54, 10080-10088. [2] B. Lewandowski, et al. Science 2013, 339, 189-193. [3] S. Kassem, A. T. L. Lee, D. A. Leigh, A. Markevicius, J. Sola, Nature Chem. 2016, 8, 138-143. [4] M. R. Wilson, J. Sol, A. Carlone, S. M. Goldup, N. Lebrasseur, D. A. Leigh, Nature 2016, 534, 235-240. [5] V. Marcos, et al. Science 2016, 352, 1555-1559.

  • 22

    invited lecture >> JCO 2016

    Jean-Marc CAMPAGNE

    ENSCM- Institut Charles Gerhardt UMR5253 Equipe AM2N8 Rue de lEcole Normale, 34296 Montpellier+(33) (0)[email protected] http://am2n.enscm.fr

    Education1990: Chemical engineer degree, Ecole Nationale Suprieure de Chimie de Montpellier1990: Master in Bioorganic Chemistry (1990, Universit Montpellier II)1991-1994: PhD (Universit Montpellier II - Dr. Jouin): Synthesis of phosphino and phosphonopeptides: haptens for the production of proteolytic catalytic antibodies.2003: D. Sc. in Chemistry (Habilitation) - Universit Paris-XI, Orsay.

    Professional positions1995-1996: Post-doctoral researcher (Stanford University (CA - USA) - Pr. B. M. Trost): Towards the total synthesis of glidobactin.1996-1998: Post-doctoral researcher (Universit de Louvain-la-Neuve (Belgium)- Pr. L. Ghosez): Peptidomimetics synthesis using Ring Closing Metathesis.1998-2005: CNRS researcher at the Institut de Chimie des Substances Naturelles de Gif sur Yvette (research director in 2005)2007: Full Professor at the Ecole Nationale Suprieure de Chimie de Montpellier

    Research activitiesNew synthetic methodologies in organic synthesis; Asymmetric Organocatalysis and Transition metal ( Cu, Fe, Pd, Au) catalysis; Natural products Synthesis

    Teaching and Administrative Activities- Teaching 192 h/year lectures and lessons for BSc and MSc students including organic chemistry, NMR, IR, MS, peptides and natural products synthesis.- Vice-President of the scientific Council (CS) of the National School of Chemistry of Montpellier (ENSCM) (2010-2012); Member of the Administration Council (CA) of the ENSCM (2012-)- PhD external examiner (38; France-Spain-Belgium-Switzerland) and habilitation external examiner- Director of the Architectures Molculaires et Matriaux Nano-structurs department (24 permanent staff + 30 non-permanent people (PhD, post-docs, trainees...); http://am2n.enscm.fr

    Selected papers1) X. Moreau, B. Bazn-Tejeda, J.-M. Campagne, Catalytic and Asymmetric Vinylogous Mukaiyama Reactions on Aliphatic Ketones: Formal Asymmetric Synthesis of Taurospongin A J. Am. Chem. Soc. 2005, 7288.2) M. Georgy, V. Boucard, J.M. Campagne, Gold(III)-Catalyzed Nucleophilic Substitution of Arylpropargylic Alcohols J. Am. Chem. Soc. 2005, 127, 14180.3) A. Parenty, X. Moreau, J.-M. Campagne, Macrolactonisations in the total synthesis of natural products, Chem. Rev. 2006, 106, 911.4) Suppo, J. S.; Subra, G.; Berges, M.; De Figueiredo R.M.; Campagne J.-M. Inverse Peptide Synthesis via Activated Aminoesters. Angew. Chem. Int. Ed. 2014, 126, 5493.5) O. Debleds, J.-M. Campagne 1,5 enyne metathesis, J. Am. Chem. Soc. 2008, 130, 1562.6) S. Drissi-Amraoui, M. Morin, C. Crevisy, O. Basle, R. Marcia de Figueiredo, M. Mauduit, JM Campagne, Angew. Chem., Int. Ed. 2015, 54, 11830.

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    invited lecture >> JCO 2016 IL 05

    INVERSE PEPTIDE SYNTHESIS VIA ACTIVATED -AMINOESTERS

    Jean-Marc CAMPAGNE

    ICGM, UMR5253, ENSCM, 8 Rue de l'Ecole Normale, 34296 Montpellier (France) [email protected], http://am2n.enscm.fr

    Peptides are attracting increasing attention on different fields such as medicinal chemistry, polymers and materials science. While these molecules are naturally built up from the NC direction, they are chemically synthesized from the opposite direction (CN). Indeed, the traditional synthesis proceeds through the activation of the carboxylic acid moiety of a first aminoacid, by means of coupling reagents, allowing the nucleophilic attack of the amino partner of a second aminoacid with concomitant formation of the amide bond (Scheme 1, a).1 Although very efficient, these coupling reagent strategies suffer from some drawbacks, notably those associated with epimerization. So, we embarked on a program aiming to synthesize amides for application in peptide synthesis via the activation of the amine function instead of the carboxylic acid (Scheme 1, b). By doing so, we wish to avoid some inherent problems found on classic peptide synthesis (e.g. epimerization) and also to approach from the natural synthesis of peptides (NC direction).

    Scheme 1: Peptide synthesis

    The use of N,N-carbonyldiimidazole (CDI) for the preparation of unprecedented activated -aminoesters, and their transformations into several dipeptides and tripeptides will be discussed (Scheme 2). 2

    Scheme 2: Dipeptide Syntheses via Activated -Aminoesters

    References: [1] Selected reviews: a) Joulli, M. M.; Lassen, K. M. ARKIVOC 2010, 189; b) El-Faham, A.; Albericio, F. Chem. Rev. 2011, 111, 6557 [2] a) Suppo, J.-S.; Subra, G.; Berges, M.; de Figueiredo, R. M.; Campagne, J.-M. Angew. Chem. Int. Ed. 2014, 53, 5389. b) Suppo, J.-S.; de Figueiredo, R. M.; Campagne, J.-M. Org. Synth. 2015, 92, 296-308.

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    invited lecture >> JCO 2016

    Richmond SARPONG

    Email: [email protected] Latimer Hall Phone: (510) 643-6312Department of Chemistry Fax: (510) 642-9675University of California, BerkeleyBerkeley, CA 94720

    Departmental and Institutional AffiliationsDepartment of Chemistry, University of California, Berkeley

    Disciplinary Field(s)Organic ChemistryOrganometallic ChemistryChemical Biology

    Educational BackgroundUndergraduate Education:Macalester College, St. Paul, MN.Bachelor of Arts Degree (Chemistry Major), May 1995 (Advisor Prof. Rebecca C. Hoye)Graduate Education:Princeton University, Princeton, NJMaster of Science Degree (Organic Chemistry), May 1997Ph. D. in Organic Chemistry, May 2001 (Advisor Prof. Martin F. Semmelhack)Postdoctoral Institution:California Institute of Technology, Pasadena, CAUNCFPfizer Postdoctoral Fellow in Organic Synthesis, 2001-2004 (Advisor Prof. Brian M. Stoltz)

    Professional Positions HeldUniversity of California, BerkeleyFull Professor, Department of Chemistry (July 2014Present)Associate Professor, Department of Chemistry (2010 June 2014)Assistant Professor, Department of Chemistry (2004 2010)

    Three Representative Publications (from 75+)1) Marth, C. J.; Gallego, G. M.; Lee, J. C.; Lebold, T. P.; Kulyk, S.; Kou, K. G. M.; Qin, J.; Lilien, R.; Sarpong, R. Network Analysis Guided Synthesis of Weisaconitine D and Liljestrandinine. Nature 2015, 528, 493498.2) Mercado-Marin, E. V.; Garcia-Reynaga, P.; Romminger, S.; Pimenta, E. F.; Romney, D. K.; Lodewyck, M. W.; Williams, D. E.; Andersen, R. J.; Miller, S. J.; Tantillo, D. J.; Berlinck, R. G. S.; Sarpong, R. Total Synthesis and Isolation of Citrinalin and Cyclopiamine Congeners. Nature 2014, 509, 318324.3) Lebold, T. P.; Wood, J. L.; Deitch, J.; Lodewyk, M. W.; Tantillo, D. J.; Sarpong, R. A Divergent Approach to the Synthesis of the Yohimbinoid Alkaloids Venenatine and Alstovenine. Nature Chem. 2013, 5, 126131.

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    invited lecture >> JCO 2016 IL 06

    STRATEGIES AND METHODS FOR CHEMICAL SYNTHESIS INSPIRED BY COMPLEX ALKALOIDS

    Richmond SARPONG

    Department of Chemistry, University of CaliforniaBerkeley, Berkeley, CA 94720 [email protected]

    Natural products continue to provide intricate problems that expose limitations in the strategies and methods employed in the synthesis of complex molecules. Several strategies and methods that have been developed in our laboratory and applied to the syntheses of architecturally complex diterpenoid alkaloids, indole alkaloids, and several Lycopodium alkaloids, will be presented and discussed.

    References: [1] Marth, C.J.; Gallego, G.M.; Lee, J.C.; Lebold, T.P.; Kulyk, S.; Kou, K.G.M.; Qin, J.; Lilien, R.; Sarpong, R.; Nature 2015, 528, 493. [2] Mercado-Marin, E.V.; Garcia-Reynaga, P.; Romminger, S.; Pimenta, E.F.; Romney, D.K.; Lodewyk, M.W.; Williams, D.E.; Andersen, R.J.; Miller, S.J.; Tantillo, D.J.; Berlinck, R.G.S.; Sarpong, R.; Nature 2014, 509, 318.

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    invited lecture >> JCO 2016

    Shuli YOU

    Vice Director, State Key Laboratory of Org