Activités de recherche

Sucres

Mots-clefs

Sucres

Enseignement

Master 1ère et 2ème année

Conférences internationales

1- Synthèse Totale de l’Huperzine A, SECO, le 25/5/00 à Houffalize
2- Sur la Route de la Fumagilline, le 22/4/03 à Montréal (UQAM)
3- On the Road to Fumagillin, le 23/4/03 à Montréal (Concordia University)
4- Two stimulating concepts in natural substances synthesis: the NEO cascade and the CIM strategy, 30 juin au 2 juillet 2010, International Conference on Medicinal Chemistry, Reims.
5- A stimulating concept in natural substances synthesis: the CIM strategy, 23 novembre 2011, Queen’s University, Belfast.
6- An efficient synthetic approach to natural products: the Claisen-Ireland/Metathesis strategy, 5 Octobre 2015, 1st Meeting of COST Action CM1407, Sapienza University, Roma.

Publications principales

1- Cyclization of Hydroxy Enol Ethers : A Stereocontrolled Approach To 3-deoxy-D-Manno-2-octulosonic Acid containing Disaccharides, A. Haudrechy and P. Sinaÿ*, J. Org. Chem., 1992, 57, 4142

2- Preferred Conformations of C-Glycosides, 14. Synthesis and Conformational Analysis of Carbon Analogs of the Blood Group Determinant H-Type II, A. Wei, A. Haudrechy, C. Audin, H.-S. Jun, N. Haudrechy-Bretel and Y. Kishi*, J. Org. Chem., 1995, 60, 2160

3- Analysis of the Diastereoselectivity of a Diels-Alder Cycloaddition through 2H NMR in chiral liquid crystals, A. Meddour, A. Haudrechy, P. Berdagué, W. Picoul, Y. Langlois and J. Courtieu, Tetrahedron: Asymmetry, 1996, 7, 2489

4- A Simple Method of Drawing Stereoisomers From Complicated Symmetrical Structures, A. Haudrechy, J. Chem. Ed., 2000, 864

5- A Formal Synthesis of (+)-Huperzin A, C. Chassaing, A. Haudrechy, C. Riche and Y. Langlois*, Tetrahedron, 2000, 56, 3181

6- A Stereoselective Formal Synthesis of Fumagillin, O. Bedel, A. Haudrechy*, Y. Langlois*, Eur. J. Org. Chem., 2004, 3813

7- Highly Enantioselective Sequential Claisen-Ireland / Metathesis: Synthesis of Cycloalkenes Bearing two Contiguous Highly Functionalized Asymmetric Centers, A. Français, O. Bedel,
W. Picoul, A. Meddour, J. Courtieu and A. Haudrechy*, Tetrahedron Asymmetry, 2005, 16, 1141

8- Diastereoselective Access to the Spirotetronate Subunit of the Quartromicins, O. Bedel*, A. Français and A. Haudrechy*, Synlett, 2005, 15, 2313

9- Selective Synthesis of a-C-(alkynyl)-Galactosides by an Efficient Tandem Reaction, S. Guillarme, K. Plé and A. Haudrechy*, J. Org. Chem., 2006, 71, 3, 1015

10- Alkynylation of Chiral Aldehydes: Alkoxy-, Amino- and Thioaldehydes, S. Guillarme, K. Plé*, A. Banchet, A. Liard and A. Haudrechy*, Chem. Reviews, 2006, 106(6); 2355

11-Quiral: a Computer Program for the Synthesis of Chiral Molecules from Sugars, J.-M. Nuzillard and A. Haudrechy, Tetrahedron Letters, 2007, 48, 13, 2311-2313

12- Is Osmylation Always Preferring the Richest Double Bond?, A. Français, O. Bedel, A. Haudrechy*, Tetrahedron, 2008, 2495

13- Molecular Dynamics Simulation Study on the Interaction of KRN 7000 and three analogues with Human CD1d, E. Hénon*, M. Dauchez, A. Haudrechy, A. Banchet, Tetrahedron, 2008, 9480

14- D-C-Mannopyranosides, M. Choumane, A. Banchet, N. Probst, S. Gérard, K. Plé*, A. Haudrechy*, Comptes Rendus de Chimie, 2011, 14, 2-3, 235

15- The stimulating adventure of KRN 7000, A. Banchet-Cadeddu, E. Hénon, M. Dauchez,J.-H. Renault, F. Monneaux,A. Haudrechy, Org. Biomol. Chem., 2011, 9, 3080

16- The Chemistry of L-Sorbose, I. Zebiri, S. Balieu, A. Guilleret, R. Reynaud, A. Haudrechy, Eur. J. Org. Chem., 2011, 16, 2905

17- A further contribution to the study of Sagittamide A: Synthesis of a pivotal intermediate belonging to a rare L-series, A. Humbert, K. Plé, D. Harakat, A. Martinez, A. Haudrechy, Molecules, 2012, 17, 7, 7709-7721

18- Stereoselective synthesis of (2S,3S,4R,5S)-2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine derivatives from L-Sorbose, S. Balieu, A. Guilleret, R. Reynaud, A. Haudrechy, Carb. Res., 2013, 374, 14-22

19- Are the furanosides that flexible? A Ring Dihedral Principal Component Analysis of furanose conformation, C. Coiffier, C. Barberot, J.-M. Nuzillard, P. Goekjian, E. Hénon, A.Haudrechy, Carbohydrate Chem., 2014, 40, 378-400.

20- From D-Xylose to a D-Glycero-L-altrose derivative, A. Banchet-Cadeddu, A. Haudrechy, Tetrahedron Lett. 2014, 55, 4605-4607.

21- Stereocontrolled Synthesis of Hydrophobic Moiety of Rhamnolipids Derivatives, B. Menhour, P. Mayon, K. Plé, S. Bouquillon, S. Dorey, C. Clément, M. Deleu, A. Haudrechy, Tetrahedron Lett. 2015, 56, 1159-1161

22- Interactions of Sugar-Based Bolaamphiphiles with Biomimetic Systems of Plasma Membranes, M. N. Nasir, J.-M. Crowet, L. Lins, F. Obounou-Akong, A. Haudrechy, S. Bouquillon, M. Deleu, Biochimie 2016, 130, 23-32

23- Recycling Mitsunobu Coupling : a Shortcut for Troublesome Esterifications, B. Menhour, F. Obounou Akong, P. Mayon, K. Plé, S. Bouquillon, S. Dorey, C. Clément, M. Deleu, D. Harakat, A. Haudrechy, Tetrahedron 2016, 72, 7488-7495

24- Differential Interaction of Synthetic Glycolipids with Biomimetic Plasma Membrane Lipids correlates with Plant Biological Response, M. N. Nasir, L. Lins, J.-M. Crowet, M. Ongena, S. Dorey, S. Dhondt-Cordelier, C. Clément, S. Bouquillon, A. Haudrechy, C. Sarazin, M.-L. Fauconnier, K. Nott, M. Deleu, Langmuir 2017, 26, 9979-9987

25 - Furanosides, synthesis and stereochemistry, P. Goekjian, A. Haudrechy, B. Menhour, C. Coiffier, Topics in Stereochemistry, 2018, Academic Press.

26 - Chimie du végétal et produits innovants à forte valeur ajoutée, A. Alabdul-Magid, C. Bliard, S. Boudesocque, S. Bouquillon, X. Coqueret, L. Dupont, F. Edwards-Lévy, S. Gérard, C. Guillermain, E. Guillon, A. Haudrechy, N. Hoffmann, J. Hubert, C. Kowandy, C. Lavaud, A. Mohamadou, M. Muzard, J.-M. Nuzillard, R. Plantier-Royon, C. Rémond, J. Sapi, S. Sayen, G. Tataru, J.-H. Renault, L’Actualité Chimique 2018, 427-428, 25-33.

27 - Synthetic Rhamnolipid Bolaforms trigger an innate immune response in Arabidopsis thaliana, W. Patricio Luzuriaga-Loaiza, R. Schellenberger, Y. De Gaetano, F. Obounou Akong, S. Villaume, J. Crouzet, A. Haudrechy, F. Baillieul, C. Clément, L. Lins, F. Allais, M. Ongena, S. Bouquillon, M. Deleu, S. Dorey, Scientific Reports (Nature Publishing) 2018, 8534.

28 - High yielding diastereoselective syn-dihydroxylation of protected HBO: an access to D-(+)-ribono-1,4-lactone and 5-O-protected a nalogues, M. Moreaux, G. Bonneau, A. Peru, F. Brunissen, M. Janvier, A. Haudrechy, F. Allais, Eur. J. Org. Chem. 2019, 7, 1600-1604.

29 - “Sugar Mapping”, a conversion concept of drawing to help the carbohydrate synthetic chemist, M.-C. Belhomme, S. Castex, A. Haudrechy, J. Chem. Ed. 2019, 2643.

30 - (S)-γ-hydroxymethyl-α,β-butenolide, a Valuable Chiral Synthon: Syntheses, Reactivity and Applications Review, A. L. Flourat, A. Haudrechy, F. Allais and J.-H. Renault, Org. Process Res. Dev. 2019, accepté. https://doi.org/10.1021/acs.oprd.9b00468

31 - Total synthesis of lignin model compounds, trimer and dihydrotrimer (β-5)-(β-O-4) of coniferylic alcohol, A. L. Flourat, A. A. M. Peru, A. Haudrechy, J.-H. Renault, F. Allais, Frontiers, 2019, accepté. https://doi.org/10.3389/fchem.2019.00842

32- Use of the Claisen/Metathesis Reaction Sequence for the Synthesis of Enantiomerically pure 1-Aminocycloalkene-1-carboxylic Acids, K. Plé, N. Probst, A. Haudrechy, Tetrahedron 2010, 66, 27, 5030-5035.

33- An Unexpected Rearrangement giving a new Thiosubstituted Carbohydrate, A. Martinez, E. Hénon, C. Coiffier, A. Banchet, D. Harakat, J.-M. Nuzillard, A. Haudrechy, Carb. Res. 2010, 345, 9, 1088-1093.

34- D-C-Mannopyranosides, M. Choumane, A. Banchet, N. Probst, S. Gérard, K. Plé, A. Haudrechy, Comptes Rendus de Chimie 2011, 14, 2-3, 235-273.

35- Drawing Chiral Mononuclear Octahedral Metal Complexes: The Case of Tripodal Ligands, A. Mohamadou, K. Plé, A. Haudrechy, J. Chem. Ed. 2011, 88, 3, 302-305.

36- Access to a new potentially bioactive C-Galactoside ester analogue of KRN 7000 by using NEO strategy, A. Banchet-Cadeddu, A. Martinez, S. Guillarme, F. Monneaux, E. Hénon, J.-H. Renault, J-M. Nuzillard, A. Haudrechy, Bioorg. Med. Chem. Lett. 2011, 21, 2510-2514.

37- The stimulating adventure of KRN 7000, A. Banchet-Cadeddu, E. Hénon, M. Dauchez, J.-H. Renault, F. Monneaux, A. Haudrechy, Org. Biomol. Chem. 2011, 9, 3080-3104.

38- The Chemistry of L-Sorbose, I. Zebiri, S. Balieu, A. Guilleret, R. Reynaud, A. Haudrechy, Eur. J. Org. Chem.2011, 16, 2905-2910.

39- Drawing Mononuclear Chiral Planar Metal Complexes, F. Chuburu, C. Cadiou, I. Dechamps, A. Haudrechy, Bulletin de l’Union des Physiciens 2011, 105, 938 (2), 7-14.

40- A further contribution to the study of Sagittamide A: Synthesis of a pivotal intermediate belonging to a rare L-series, A. Humbert, K. Plé, D. Harakat, A. Martinez, A. Haudrechy, Molecules 2012, 17, 7, 7709-7721.

41- Stereoselective synthesis of (2S,3S,4R,5S)-2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine derivatives from L-Sorbose, S. Balieu, A. Guilleret, R. Reynaud, A. Haudrechy, Carb. Res. 2013, 374, 14-22.

42- Are the furanosides that flexible? A Ring Dihedral Principal Component Analysis of furanose conformation, C. Coiffier, C. Barberot, J.-M. Nuzillard, P. Goekjian, E. Hénon, A. Haudrechy, Carbohydrate Chem. 2014, 40, 378-400.

43- From D-Xylose to a D-Glycero-L-altrose derivative, A. Banchet-Cadeddu, A. Haudrechy, Tetrahedron Lett. 2014, 55, 4605-4607.

44- Stereocontrolled Synthesis of Hydrophobic Moiety of Rhamnolipids Derivatives, B. Menhour, P. Mayon, K. Plé, S. Bouquillon, S. Dorey, C. Clément, M. Deleu, A. Haudrechy, Tetrahedron Lett. 2015, 56, 1159-1161.

45- Interactions of Sugar-Based Bolaamphiphiles with Biomimetic Systems of Plasma Membranes, M. N. Nasir, J.-M. Crowet, L. Lins, F. Obounou-Akong, A. Haudrechy, S. Bouquillon, M. Deleu, Biochimie 2016, 130, 23-32.

46- Recycling Mitsunobu Coupling : a Shortcut for Troublesome Esterifications, B. Menhour, F. Obounou Akong, P. Mayon, K. Plé, S. Bouquillon, S. Dorey, C. Clément, M. Deleu, D. Harakat, A. Haudrechy, Tetrahedron 2016, 72, 7488-7495.

47- Differential Interaction of Synthetic Glycolipids with Biomimetic Plasma Membrane Lipids correlates with Plant Biological Response, M. N. Nasir, L. Lins, J.-M. Crowet, M. Ongena, S. Dorey, S. Dhondt-Cordelier, C. Clément, S. Bouquillon, A. Haudrechy, C. Sarazin, M.-L. Fauconnier, K. Nott, M. Deleu, Langmuir 2017, 26, 9979-9987.

48- Chimie du végétal et produits innovants à forte valeur ajoutée, A. Alabdul-Magid, C. Bliard, S. Boudesocque, S. Bouquillon, X. Coqueret, L. Dupont, F. Edwards-Lévy, S. Gérard, C. Guillermain, E. Guillon, A. Haudrechy, N. Hoffmann, J. Hubert, C. Kowandy, C. Lavaud, A. Mohamadou, M. Muzard, J.-M. Nuzillard, R. Plantier-Royon, C. Rémond, J. Sapi, S. Sayen, G. Tataru, J.-H. Renault, L’Actualité Chimique 2018, 427-428, 25-33.

49- Synthetic Rhamnolipid Bolaforms trigger an innate immune response in Arabidopsis thaliana, W. Patricio Luzuriaga-Loaiza, R. Schellenberger, Y. De Gaetano, F. Obounou Akong, S. Villaume, J. Crouzet, A. Haudrechy, F. Baillieul, C. Clément, L. Lins, F. Allais, M. Ongena, S. Bouquillon, M. Deleu, S. Dorey, Scientific Reports (Nature Publishing, 2018, 8534). 10.1038/s41598-018-26838-y

50- High yielding diastereoselective syn-dihydroxylation of protected HBO: an access to D-(+)-ribono-1,4-lactone and 5-O-protected a nalogues, M. Moreaux, G. Bonneau, A. Peru, F. Brunissen, M. Janvier, A. Haudrechy, F. Allais, Eur. J. Org. Chem. 2019, 7, 1600-1604.

51- “Sugar Mapping”, a conversion concept of drawing to help the carbohydrate synthetic chemist, M.-C. Belhomme, S. Castex, A. Haudrechy, J. Chem. Ed. 2019, 96, 11, 2643-2648.

52- (S)-γ-hydroxymethyl-α,β-butenolide, a Valuable Chiral Synthon: Syntheses, Reactivity and Applications Review, A. L. Flourat, A. Haudrechy, F. Allais and J.-H. Renault, Org. Process Res. Dev. 2019, 24, 5, 615-636.

53- Total synthesis of lignin model compounds, trimer and dihydrotrimer (β-5)-(β-O-4) of coniferylic alcohol, A. L. Flourat, A. A. M. Peru, A. Haudrechy, J.-H. Renault, F. Allais, Frontiers, 2019, 7, 842.

54- Accessing p-Hydroxycinnamic acids: chemical synthesis, biomass recovery or engineered microbial production? A. L. Flourat, J. Combes, C. Bailly-Maitre-Grand, A. Haudrechy, J.-H. Renault, F. Allais, ChemSusChem, 2021, 14, 118-124. http://dx.doi.org/10.1002/cssc.202002141.

55- Un bon croquis vaut mieux qu’un long discours ? (A good sketch is better than a long speech?), J. Juvin, M.-C. Belhomme, S. Castex, C. Bliard, A. Haudrechy, Notes Académiques de l'Académie d'agriculture de France 2021, 2, 1-9.

56- Rhamnolipids and their 3-(3-hydroxyalkanoyloxy)alkanoic acid precursors activate Arabidopsis innate immunity through two independent mechanisms, R. Schellenberger, J. Crouzet, A. Nickzad, A. Kutschera, T. Gerster, N. Borie, C. Dawid, M. Cloutier, S. Villaume, S. Dhondt-Cordelier, J. Hubert, S. Cordelier, F. Mazeyrat-Gourbeyre, C. Schmid, M. Ongena, J.-H. Renault, A. Haudrechy, T. Hofmann, F. Baillieul, C. Clément, C. Zipfel, C. Gauthier, E. Déziel, S. Ranf, S. Dorey, Proc. Natl. Acad. Sci. U.S.A. 2021, 118 (39), e2101366118.

57- A stereo-electronic interpretation of a challenging orthoamide Overman rearrangement rationalized by molecular modelling, J. Juvin, V. Malherbe, M.-C. Belhomme, S. Castex, A. A. Martinez, H. Khartabil, A. Haudrechy, New J. Chem. 2022, 46, 17175-17182.

Prix, récompenses

Prix Dina Surdin 91 (prix national de thèse de la Division de Chimie Organique de la Société Française de Chimie)