David GUEYRARD

 Dr David GUEYRARD (MCF)

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04 72 44 83 49

2008 : Habilitation à Diriger les Recherches (HDR), Université Claude Bernard Lyon 1
2003 - Present : Assistant Professor (MCF), Université Claude Bernard Lyon 1
2002 - 2003 : ATER, Université Rennes 1 (Dr Bernard Boitrel)
2001 - 2002 : ATER, Université d’Orléans (Prof. Philippe Compain / Prof. Olivier R. Martin)
2000 - 2001 : Postdoctoral studies, University College of London (Prof. Charles M. Marson)
1997 - 2000 : PhD in Organic Chemistry, Université d’Orléans (Prof. Patrick Rollin)


1) D. Gueyrard, C. Lorin, J. Moravcova, P. Rollin* : A new intramolecular migration in thiosugar chemistry : S  O transfer of a benzothiazol-2-yl group in saccharidic sulfones, J. Carbohydr. Chem., 1999, 18, 3, 317-331.

2) R. Iori*, R. Bernardi, D. Gueyrard, P. Rollin, S. Palmieri : Formation of glucoraphanin by chemoselective oxidation of natural glucoerucin : a chemoenzymatic route to sulforaphane, Bioorg. Med. Chem. Lett., 1999, 9, 7, 1047-1048.

3) D. Gueyrard, P. Rollin*, Truong T. T. N., M. Ourévitch, J. P. Bégué, D. Bonnet-Delpon : A convenient synthesis of fluoroalkyl and fluoroarylglycosides using Mitsunobu conditions, Carbohydr. Res., 1999, 318, 1-4, 171-179.

4) D. Gueyrard, A. Tatibouët, Y. Gareau, P. Rollin* : A novel « one-pot » synthesis of thiosugar-derived S-xanthates, Org. Lett., 1999, 1, 3, 521-522.

5) V. Aucagne, D. Gueyrard, A. Tatibouët, S. Cottaz, H. Driguez, M. Lafosse, P. Rollin* : The first synthesis of C-glucotropaeolin, Tetrahedron Lett., 1999, 40 (41), 7319-7321.

6) O. Leoni, R. Bernardi, D. Gueyrard, P. Rollin*, S. Palmieri : Chemo-enzymatic preparation from renewable resources of enantiopure 1,3-oxazolidine-2-thiones, Tetrahedron : Asymm., 1999, 10 , 24, 4775-4780.

7) D. Gueyrard, V. Grumel, O. Leoni, S. Palmieri, P. Rollin* : Reactivity range of a chiral 1,3-oxazolidine-2-thione obtained from vegetable source through chemo-enzymatic processing, Heterocycles, 2000, 52, 2, 827-843.

8) V. Aucagne, D. Gueyrard, A. Tatibouët, A. Quinsac, P. Rollin* : Synthetic approaches to C - analogues of glucosinolates, Tetrahedron, 2000, 56, 17, 2647-2654.

9) D. Gueyrard, R. Iori, S. Palmieri, P. Rollin* : First synthesis of an O-glycosylated glucosinolate isolated from Moringa oleifera, Tetrahedron Lett., 2000, 41, 8307-8309.

10) J. Girniene, D. Gueyrard, A. Tatibouët*, A. Sackus, P. Rollin : Base-modified nucleosides from carbohydrate derived oxazolidinethiones : a five-step process, Tetrahedron Lett., 2001, 42, 2977-2980.

11) D. Gueyrard, O. Leoni, S. Palmieri, P. Rollin* : A new and rapid access to homochiral 2,3-dihydro-oxazolo[2,3-b]quinazolin-5-ones, Tetrahedron: Asymm., 2001, 12, 337-340.

12) J. Barillari, D. Gueyrard, P. Rollin, R. Iori* : Barbarea verna as a source of 2-phenylethyl glucosinolate, precursor of cancer chemopreventive phenylethyl isothiocyanate, Fitoterapia, 2001, 72, 760-764.

13) J-Y. Goujon, D. Gueyrard, P. Compain*, O. R. Martin*, N. Asano: Ring-opening reactions of iminosugars-based aziridines: application to the general synthesis of -1-C-substituted derivatives of fagomine, Tetrahedron: Asymmetry, 2003, 14, 1969-1972.

14) C. Ruzie, D. Gueyrard, B. Boitrel* : Synthesis of 5,10,15,20-tetrakis(2-amino-5-methoxyphenyl)-porphyrin: a versatile building block for porphyrin side selection, Tetrahedron Lett., 2003, 45, 1713-1716.

15) D. Gueyrard, A. Didier, C. Ruzie, A. Bondon, B. Boitrel*: Synthesis of tripodal phenol porphyrins: a modular approach to mimic - enzymes with a cross-linked tyrosine, Synlett, 2004, 7, 1158-1162.

16) J-Y. Goujon, D. Gueyrard, P. Compain*, O. R. Martin*, K. Ikeda, A. Kato, N. Asano: General synthesis and biological evaluation of α-1-C-substituted derivatives of fagomine (2-deoxynojirimycin--C-glycosides), Bioorg. Med. Chem., 2005, 13, 2313-2324.

17) D. Gueyrard*, R. Haddoub, A. Salem, N. Said Bacar, P. G. Goekjian: Synthesis of methylene exoglycals using a modified Julia olefination, Synlett, 2005, 3, 520-522.

18) A. Bourderioux, M. Lefoix, D. Gueyrard, A. Tatibouet*, S. Cottaz, S. Arzt, W.P. Burmeister, P. Rollin : The glucosinolate-myrosinase system. New insights into enzyme-substrate interactions by use of simplified inhibitors, Org. Biomol. Chem., 2005, 3, 1872-1879.

19) M. J. Bourgeois, D. Gueyrard, E. Montaudon, P. Rollin* : Exploration of synthetic pathways to unprecedented terpenyl thioglycosides, Letters in Organic Chemistry, 2005, 2, 665-667.

20) D. Gueyrard*, P. Fontaine, P. G. Goekjian : Synthesis of C-glucosides endo-glycals from C-glucosyl vinyl sulfones, Synthesis, 2006, 9, 1499-1503.

21) M. Benltifa, S. Vidal, D. Gueyrard, P. G. Goekjian, M. Msaddek, J. P. Praly*: 1,3-Dipolar cycloaddition reactions on carbohydrate-based templates: synthesis of spiro-isoxazolines and 1,2,4-oxadiazoles as glycogen phosphorylase inhibitors, Tetrahedron Lett., 2006, 47, 6143-6147.

22) C. Schneider, D. Gueyrard, F. Popowycz, B. Joseph, P. G. Goekjian*: Synthesis of 6-subtituted pyrido[2,3-b]indoles by electrophilic substitution, Synlett, 2007, 14, 2237-2241.

23) K. Aouadi, B. Defaut, P. G. Goekjian, D. Gueyrard*: Synthesis of semicyclic dienes by modified Julia olefination of vinyl sulfones derived from carbohydrates, Synlett, 2007, 16, 2590-2592.

24) B. Bourdon, M. Corbet, P. Fontaine, P. G. Goekjian, D. Gueyrard* : Synthesis of enol ethers from lactones using modified Julia olefination reagents: application to the preparation of tri-and tetrasubstituted exoglycals, Tetrahedron Lett., 2008, 49, 747-749.

25) M. Corbet, B. Bourdon, D. Gueyrard*, P. G. Goekjian* : A Julia olefination approach to the synthesis of functionalized enol ethers and their transformation into carbohydrate-derived spiroketals, Tetrahedron Lett., 2008, 49, 750-754.

26) R. Haddoub, D. Gueyrard, P. G. Goekjian*: Synthesis of C-Linked Immobilized Analogs of Aloisine A by "Click" Chemistry, Tetrahedron Lett., 2009, 50, 741-744.

27) C. Schneider, D. Gueyrard, B. Joseph, P. G. Goekjian*: Chemoselective functionalization of alpha carbolines at C-2, C-3, C-4 and C-6 positions using Suzuki–Miyaura reactions, Tetrahedron, 2009, 65, 5427-5437.

28) C. Corbel, R. Haddoub, D. Guiffant, O. Lozach, D. Gueyrard, J. Lemoine*, M. Ratin, L. Meijer, S. Bach*, P. G. Goekjian*: Identification of potential cellular targets of Aloisine A by affinity chromatography, Bioorg. Med. Chem., 2009, 17, 5572-5582.

29) M. Benltifa, M. De Kiss, M.I. Garcia-Moreno, C. Ortiz-Mellet, D. Gueyrard*, A. Wadouachi*: Regioselective synthesis and biological evaluation of spirosulfamidates glycosides from exoglycals, Tetrahedron: Asymm., 2009, 20, 1817-1823.

30) M. Benltifa, J.M. Hayes, S. Vidal, D. Gueyrard, P. G. Goekjian, J. P. Praly*, G. Kizilis, C. Tiraidis, K.M. Alexacou, E.D. Chrysina*, S.E. Zographos, D.D. Leonidas, G. Archontis, N.G. Oikonomakos: Glucose based spiro-isoxazolines: A new family of potent glycogen phosphorylase inhibitors, Bioorg. Med. Chem., 2009, 17, 7368-7380.

31) D. Goyard, S. M. Telligmann, C. Goux-Henry, M. M. K. Boysen, E. Framery, D. Gueyrard, S. Vidal*: Carbohydrate-based spiro-(bis)isoxazolines: Synthesis and evaluation in asymmetric synthesis, Tetrahedron Lett., 2010, 51, 374-377.

32) J. Schleiss, D. Cerniauskaite, D. Gueyrard, R. Iori, P. Rollin, A. Tatibouet*: Thioimidates N-oxides: From nature to synthetic pathways, Synlett, 2010, 725-728.

33) D. Gueyrard*, R. Iori, A. Tatibouet, P. Rollin : Glucosinolate Chemistry: Synthesis of O-glycosylated derivatives of Glucosinalbin, Eur. J. Org. Chem., 2010, 3657-3664.

34) L. Tomas, D. Gueyrard*, P.G. Goekjian* : Synthesis of the spiroketal fragment of bistramide A via an exocyclic enol ether, Tetrahedron Lett., 2010, 51, 4599-4601.

35) C. Schneider, D. Goyard, D.Gueyrard, B. Joseph, P. G. Goekjian* : Synthesis of 2-, 3- and 4-substituted pyrido[2,3-b]indoles by C-N, C-O ans C-C (sp)bond formation, Eur. J. Org. Chem., 2010, 6665-6677.

36) D. Gueyrard, R. Tlegenov, S. Steinbruckner, B. Perly, P. Rollin* : Synthesis of new derivatives of 11-thiolupinine, J. Sulfur Chem., 2010,31, 493-498.

37) L. Tomas, T. Bechet, E. Jeanneau, D. Gueyrard*, P. G. Goekjian* : Efficient Synthesis of the C1-C13 Fragment of Bistramide A, Synlett., 2012, 51, 215-218.

38) H. Abda, K. Aouadi, D. Gueyrard, J. P. Praly, M. Msaddek*: Study of the Regio- and Stereoselectivity of [3+2] Cycloaddition of Nitrile Oxides to Various Racemic 3-acyloxy and 3-hydroxybut-1-enes, Letters in Organic Chemistry, 2012, 9, 96-100.

39) T. Tite, L. Tomas, T. Docsa, P. Gergely, J. Kovensky, D. Gueyrard*, A. Wadouachi*: Synthesis of N-aryl spiro-sulfamides as potential glycogen phosphorylase inhibitors, Tetrahedron Lett., 2012, 53, 959-961.

40) L. Tomas, G. Boije Af Gennas, M. A. Hiebel, P. Hampson, D. Gueyrard, B. Pelotier, J. Yli-Kauhaluoma, O. Piva, J. M. Lord*, P. G. Goekjian*: Total Synthesis of Bistramide A and Its 36(Z) Isomers: Differential Effect on Cell Division, Differentiation, and Apoptosis, Chem. Eur J., 2012, 18, 7452-7466.

41) L. Tomas, B. Bourdon, J. C. Caille, D. Gueyrard*, P. G. Goekjian*: A concise and efficient synthesis of spiroketals. Application to the synthesis of Spiket P and a spiroketal from Bactrocera species, Eur. J. Org. Chem., 2013, 915-920.

42) S. Habib, F. Larnaud, E. Pfund, T. Lequeux, B. Fenet, P. G. Goekjian, D. Gueyrard*: Synthesis of fluorinated exo-Glycals through Modified Julia Olefination, Eur. J. Org. Chem., 2013, 1872-1875.

43) S. Habib, F. Larnaud, E. Pfund, T. Mena Barragan, T. Lequeux, C. Ortiz Mellet, P. G. Goekjian, D. Gueyrard*: Synthesis of substituted exo-glucals via a modified Julia olefination and identification as selective β-glucosidase inhibitors, Org. Biomol. Chem., 2014, 12, 690-699.

44) S. Tardy, A. Orsato, L. Mologni, W. H. Bisson, C. Donadoni, C. Gambacorti-Passerini, L. Scapozza, D. Gueyrard, P. G. Goekjian* : Synthesis and biological evaluation of benzo[4,5]imidazo[1,2-c]pyrimidine and benzo[4,5]imidazo[1,2-a]pyrazine derivatives as anaplastic lymphoma kinase inhibitors, Bioorg. Med. Chem., 2014, 22, 1303-1312.

45) N. Gigant, S. Habib, M. Medoc, P. G. Goekjian, D. Gueyrard*, I. Gillaizeau*: Synthesis of exo-enamides from protected lactams using a modified Julia olefination reaction: application to the synthesis of spiroaminal fragments, Eur. J. Org. Chem., 2014, 6501-6506.

46) S. Habib, D. Gueyrard*: Modified Julia olefination on sugar-derived lactones: synthesis of difluoro-exo-glycals, Eur. J. Org. Chem., 2015, 871-875.

47) E. Pfund, T. Lequeux*, D. Gueyrard* : Synthesis of fluorinated and CF3 substituted alkenes through the modified Julia olefination: an update, Synthesis, 2015, 1534-1546.

48) C. Le Guen, T. Mena Barragan, C. Ortiz Mellet, D. Gueyrard, E. Pfund, T. Lequeux*: Fluorinated hydroxypiperidines as selective β-glucosidase inhibitors, Org. Biomol. Chem., 2015, 13, 5983-5996.

49) M. Cheniour, D. Gueyrard, P. G. Goekjian, T. Granjon, O. Marcillat*: A convenient and versatile synthesis of Laurdan-like fluorescent membrane probes: characterization of their fluorescence properties, RSC Adv., 2016, 5, 5547-5557.

50) H. V. Trinh, L. Perrin*, P. G. Goekjian, D. Gueyrard*: Development of a modified Julia olefination of imides for the synthesis of alkaloids, Eur. J. Org. Chem., 2016, 2944-2953.

51) N. Dussart, H. V. Trinh, D. Gueyrard*: Modified Julia Olefination on Anhydrides: Extension and Limitations. Application to the Synthesis of Maculalactone B, Org. Lett., 2016, 18, 4790-4793.

52) C. Adouama, R. Keyrouz, G. Pilet, C. Monnereau, D. Gueyrard, T. Noel, M. Médebielle* : Access to cyclic gem-difluoroacyl scaffolds via electrochemical and visible light photocatalytic radical tandem cyclization of heteroaryl chlorodifluoromethyl ketones, Chem. Commun., 2017, DOI: 10.1039/C7CC02979A.