VOGEL Pierre, Hon. Prof.

photo pierre vogel

Pierre Vogel was born in Cully (Switzerland) Oct. 23, 1944. In 1969, he did his Ph.D under supervision of Prof. H. Prinzbach at the Institute of Organic Chemistry, University of Lausanne (UNIL). He spent two years at Yale University, New Haven, Conn., USA with Prof. Martin Saunders, Prof. Jerome. A. Berson, Kenneth. A. Wiberg and Paul.v.R. Schleyer (Princeton University). He worked then as a Research chemist at Syntex S.A., in Mexico-City with Prof. Pierre Crabbé before the return to the University of Lausanne in 1973. As of 1977 he became Professor of organic chemistry at the University of Lausanne. He was also part-time doctoral school teacher at the Universities of Rouen and Caen from 1991 to 1993 and part-time professor at Ecole Polytechnique in Palaiseau (France) from 1993-2000.

In 1992 he has been Pacific Coast (USA) Lecturer. He has been invited professor at the Universities of Montpellier, Paris-Sud and the Ecole Supérieure de physique et de chimie industrielles de la ville de Paris (ParisTech). He also tough at the Universidad Complutense in Madrid. He has been Novartis Distinguished lecturer in 2003 and Boeringer Lecturer in 2005. Since 2001 he is Professor of organic chemistry at the EPFL and has been the Director of the doctoral program in chemistry and chemical engineering of the EFPL between 2002 until 2010. Since 2011 he is honorary professor of the EPFL and is responsible of the medicinal chemistry laboratory of the Ludwig Institute for Cancer Research, in collaboration with the EPFL. He participates to the European FP7 health program on pancreas cancer. More than 525 publications in refereed journals, 8 patents and 3 books.

TOPICS OF INTEREST AND SELECTED LATEST PUBLICATIONS

Combinatorial and asymmetric synthesis of natural products and analogues of biological interest, especially the anti-cancer anthracyclines, polyketide and polypropionate antibiotics.

  • Total Synthesis and Determination of the Absolute Configuration of (-)-Dolabriferol. Laclef, S.; Turks, M.; Vogel. P. Angew. Chem. Int. Ed. 2010, 49, 8535-8527.
  • Efficient Asymmetric Synthesis of Long-Chain Polyketides Containing up to Ten Contiguous Stereogenic Centres by Double Chain Elongation. Turks, M.; Fairweather, K. A.; Scopelliti, R.; Vogel, P. Eur. J. Org. Chem. 2011, 3317-3328.
  • Concise Synthesis of Complicated Polypropionates through One-Pot Dissymmetrical Two-Directional Chain Elongation. Exner, C. J; Turks, M.; Fonquerne, F.; Vogel, P. Chem. Eur. J. 2011, 17 4246-4253.
  • Total Asymmetric Syntheses of ß-Hydroxy-δ-lactones via Umpolung with Sulfur Dioxide. Exner, C. J.; Laclef, S.; Poli, F.; Turks, M.; Vogel, P. J. Org. Chem. 2011, 76, 840-845.
  • Short  Diastereoselective Synthesis of the C1-C13 (AB Spiroacetal) and C17-C28 Fragments (CD Spiroacetal) of Spongistatin 1 and 2 through Double Chain-Elongation Reactions. Flowers, C.; Vogel, P. Chem. Eur. J. 2010, 16, 14074-14082.
  • Combinatorial Synthesis of Linearly Polycyclic Compounds, Including Anthracyclinones, through Tandem Diels-Alder Additions. Vogel, P. Topics in Current Chemistry (Springer Verlag) 2008, 282, 187-214.
  • Use of Sultines in the Asymmetric Synthesis of Polypropionate Antibiotics, Vogel, P.; Turks, M.; Bouchez, L.; Craita, C.; Huang, X.; Murcia, M. C.; Fonquerne, F.; Didier, C.; Flowers, C. Pure Appl. Chem. 2008, 80, 791-805.
  • Short Synthesis of the C16-C28 Polyketide Fragment of Apoptolidin A aglycone. Craita, C.; Didier, C.; Vogel. P. Chem. Commun. 2007, 2411-2413.
  • Asymmetric Synthesis of the Polyol Subunit of the Polyene Macrolide Antibiotic RK-397. Gerber-Lemaire, S.; Carmona, A. T.; Meilert, K. T.; Vogel. P. Eur. J. Org. Chem. 2006, 891-900.
  • Expeditious Asymmetric Synthesis of a Stereoheptad Corresponding to the C(19)-C(27)-Ansa Chain of Rifamycins: Formal Total Synthesis of Rifamycin S. Turks, M.; Huang, X. Vogel. P. Chem. Eur. J. 2005, 11, 465-476.
  • First Asymmetric Synthesis of the Cyclohexanone Subunit of Baconipyrones A and B. Revision of Its Structure. Turks, M.; Murcia, M. C.; Scopelliti, R.; Vogel. P. Org. Lett. 2004, 6, 3031-3034.

Glycomimetics as potential drugs and anti-cancer vaccines.

  • Anti-Cancer Activity of 5-O-Alkyl-1,4-dideoxy-1,4-iminoribitols. Bello, C.; Dal Bello, G.; Cea, M.; Nahimana, A.; Aubry, D.; Moran, E.; Fruscione, F.; Pronzato, P.; Grossi, F.; Patrone, F.; Ballestrero, A.; Dupuis, M.; Sordat, B.; Zimmermann, K.; Loretan, J.; Wartmann, M.; Duchosal, M. A.; Nencioni, A.; Vogel. P. Biorg. Med. Chem. 2011.
  • Novel 2-[(benzylamino)methyl]pyrrolidine-3,4-diol Derivatives as α-Mannosidase Inhibitors and with anti-tumor Activities against Hematological and Solid Malignancies. Bello, C.; Cea, M.; Dal Bello, G.; Garuti, A.; Rocco, I.; Cirmena, G.; Moran, E.; Nahimana, A.; Duchosal, M. A.; Fruscione, F.; Fronzato, P.; Grossi, F.; Patrone, F.; Ballestrero, A.; Dupuis, M.; Sordat, B.; Necioni, A.; Vogel, P. Bioorg. Med. Chem. 2010, 18, 3320-3334.
  • Structural Insights into the Specificity of Xyn10B from Paenibacillus barcinonensis and its Improved Stability by Force Protein Evolution. Gallardo, O.; Pastor, F. I. J.; Polaina, J.; Diaz P.; Lysek, R.; Vogel, P. Sorma, P.; Gonzalez, B.; Sanz-Aparicio, J. J. Biol. Chem. 2010, 285, 2721-2733.
  • Synthesis of Novel Pyrrolidine 3,4-diol Derivatives as Inhibitors of α-L-Fucosidases, Moreno-Clavijo, E.; Carmona, A. T.; Vera-Ayoso, Y.; Moreno-Vargas, A.. J.; Bello, C.; Vogel, P.; Robina. I. Org. Biomol. Chem. 2009, 7, 1192-1202.
  • Synthesis and Conformational Analysis of (α-D-galactosyl)-phenylmethane and α-, β-difluoromethane analogs: Interactions with the Plant Lectin Viscumin. Kolympadi, M.; Fontanella, M.; Ventut ri, C.; Andre, S.; Gabius H.-J.; Jimenez-Barbero, J.; Vogel. P. Chem. Eur. J. 2009, 15, 2861-2873.
  • Synthesis and L-Fucosidase Inhibitory Potency of a Cyclic Sugar Imine ant its Pyrrolidine Analog. Behr, J.-B., Paerson, M. S. M.; Bello, C.; Vogel, P.; Plantier-Royon, R. Tetrahedron Asymmetry 2008, 19, 1829-1832.
  • New Synthetic Seven-membered 1-Azasugars Displaying Potent Inhibition towards Glycosidases and Glucosylceramidetransferase. Li, H.; Liu, T.; Zhang, Y.; Favre, S.; Bello, C.; Vogel, P.; Butters, T. D.; Oikonomakos, N. G.; Marrot, J.; Blériot, Y. ChemBioChem. 2008, 9, 253-260..
  • Imino-C-disaccharides and analogs: synthesis and biological activity. Vogel, P.; Gerber-Lemaire, S.; Juillerat-Jeanneret, L. in “Iminosugars” Eds.: Compain, P.; Martin, O. R., John Wiley & Sons Ltd. Chichester, UK 2007, p. 87-130.
  • The Use of Levoglucosenone and Isoglucoseneone as templates for the Construction of C-linked Disaccharides. Awad, L.; Demange, R.; Zhu, Y.-H.; Vogel, P. Carbohydrate. Research. 2006, 341, 1235-1252.
  • Synthesis of Amino- and Diaminoconduritols and their Applications. Lysek, R.; Vogel. P. Tetrahedron 2006, 62 2733-2768.

New organic chemistry based on pericyclic reactions of sulfur dioxide

  • BCl3-Mediated Ene Reaction of Sulfur Dioxide and Unfonctionalized Alkenes. Markovic, D.; Volla, C. N. R.; Vogel, P.; Varela-Alvarez, A.; Sordo, J. A. Chem. Eur. J. 2010, 16, 5969-5975.
  • Desulfinylation of prop-2-enesulfinic Acid: Experimental Results and Mechanistic Theoretical Analysis. Varela- Alvarez, A.; Markovic, D.; Vogel, P.; Sordo, J. A. J. Am. Chem. Soc. 2009, 131, 9547-9561.
  • Umpolung with Sulfur Dioxide: Carbon-Carbon Cross-coupling of Electron-rich 1,3-Dienes and Alkenes: Application to the Enantioselective Synthesis of Long-chain Polyketide Fragments. Turks, M.; Exner, C. J.; Hamel, C.; Vogel. P. Synthesis 2009, 1065-1074.
  • New Organic Chemistry of Sulfur Dioxide. Vogel, P.; Turks, M.; Bouchez, L., Markovic, D.; Varela-Alvarez, A.; Sordo, J. A. Acc. Chem. Res. 2007, 40, 931-942.
  • Sulfur Dioxide Mediated One-pot, Four Component Synthesis of Polyfonctional Sulfones and Sulfonamides, including Medium-ring Cyclic Derivatives. Bouchez. L. C.; Turks. M.; Dubbaka, S. R.; Fonquerne, F.; Craita, C.; Laclef, S.; Vogel. P. Tetrahedron 2005, 61, 11473-11487.

New catalyzed carbon-carbon bond forming reactions. Use of iron catalysts for more sustainable processes

  • The Catalyzed Desulfinylative Allylation of Carbonyl Compounds with Alk-2-enesulfonyl Chlorides and Silyl Alk-2-enesulfinates. Volla, C. M. R.; Markovic, D.; Laclef, S.; Vogel. P. Chem. Eur. J. 2010, 16, 8984-8988.
  • Ligandless Iron-Catalyzed Desulfinylative C-C Allylation Reactions using Grignard Reagents and Alk-2-enesulfonyl Chlorides. Volla, C. M. R. Markovic, D.; Dubbaka, S. R.; Vogel. P. Eur. J. Org. Chem. 2009, 6281-6288.
  • Chemoselective C-H Bond Activation: Ligand and Solvent Free Iron-Catalyzed Oxidative C-C Cross-Coupling of tertiary Amines with Terminal Alkynes. Reaction Scope and Mechanism. Volla, C. M. R.; Vogel. P. Org. Lett. 2009, 11, 1701-1704.
  • Iron-catalyzed Mizoroki-Heck Cross-Coupling reaction with Styrenes. Loska, R.; Volla, C. M. R.; Vogel. P. Adv. Synth. Catal. 2008, 350, 2859-2864.
  • Iron/copper-Catalyzed C-C Cross-Coupling of Aryl Iodides with Terminal Alkynes. Volla, C. M. R.; Vogel. P. Tetrahedron Lett. 2008, 49, 5961-5964.
  • Iron-Catalyzed Desulfinylative C-C Cross-Coupling Reactions of Sulfonyl Chlorides with Grignard Reagents. Volla, C. M. R.; Vogel. P. Angew. Chem. Int. Ed. 2008, 47, 1305-1307.
  • Organosulfur Compounds: Electrophilic reagents in Transition-metal-Catalyzed Carbon-Carbon Bond-forming Reactions. Dubbaka, S. R.; Vogel. P. Angew. Chem. Int. Ed. 2005, 44, 7674-7684.

Theoretical and Computational Chemistry

  • The Norbornene Mystery Revealed. Steimann, S. N.; Vogel. P.; Mo, Y.; Corminboeuf, C. Chem. Commun. 2011, 227-229;
  • Quantum Calculations on the Acid-Catalyzed Rearrangements of Norborn-5-en-2-one, 7-Oxanorborn-5-en-2-one and 7-Azanorborn-5-en-2-one. Sordo, J. A.; Varela-Alvarez, A.; Giani, S.; Vogel. P.Appl. Catal. A. General. 2008, 336, 72-78.
  • Hetero-Diels-Alder and Cheletropic Additions of Sulfur Dioxide to Conjugated Dienes. Experimental Facts and Theoretical Analysis. Vogel, P.; Sordo, J. A. Current Organic Chemistry 2006, 10, 2007-2036.
  • Mechanism of the Diphenyldisulfone-Catalyzed Isomerization of Alkenes. Origin of the Chemoselectivity: Experimental and Quantum Chemistry Studies. Markovic, D.; Varela-Alvarez, A.; Sordo, J. A.; Vogel. P. J. Am. Chem. Soc. 2006, 128, 7782-7795.
  • Equilibrium and Kinetic Deuterium Isotope Effects on the hetero-Diels-Alder Addition of Sulfur Dioxide. Monnat, F. Vogel,P.; Meana, R.; Sordo, J. A. Angew. Chem. Int. Ed. 2003, 42, 3924-3927.

BOOKS

P. Vogel,” La Réactivité Chimique”, Editions Georgi, St-Saphorin, 1979, ISBN 2 604 00041 5
P. Vogel,” Carbocation Chemistry”, Elsevier, Amsterdam, 1985, ISBN 0-444-42522-5
P. Vogel, “Chimie organique: Méthodes et Modèles” DeBoeck Université, Paris, Bruxelles, 1997, ISBN 2-8041-2620-X