Jacques LEBRETON

Organic chemistry

With these colleagues Drs. Monique Mathé-Allainmat and Fabrice Dénès their major research interests are medicinal chemistry and total synthesis including the development of synthetic methods based on organometallic or radical reactions. Most of their recent work has focused on the synthesis of bioactive molecules, such as steroids, nucleosides, alkaloids, azasugars and marine natural products for biological evaluation purposes in the fields of HIV, central nervous system diseases, cancer and drug delivery through academic and industrial collaborations. Their research efforts also include the synthesis of labeled molecules to study biological processes.

Jacques Lebreton was born in Guérande (France) in 1960. He received his Ph.D. degree (1986) from the University of Paris XI-Orsay under the supervision of Professor Eric Brown (Le Mans). His thesis work included the total synthesis of C-nor D-homosteroids. In 1986, he began his first post-doctoral fellowship with Professor James A. Marshall at the University of South Carolina working on the [2,3]-Wittig rearrangement and its application in total synthesis. Following a second post-doctoral fellowship with Professor Robert E. Ireland at the University of Virginia working on the total synthesis of monensine, he joined the laboratories of CIBA-GEIGY (Novartis) in Basle in 1990, where he worked in Dr. Alain De Mesmaeker's group in the field of antisense. In 1994, he joined the CNRS and spent a few years in the group of Dr. Jean Villiéras (UMR-CNRS 6513, Nantes) concerned with organometallic chemistry. In 1998, he was promoted to Professor at the University of Nantes. In 2000 with his friend and colleague André Guingant, he set up a research group, named Symbiose, devoted to developing research at the interface between chemistry and biology. In 2005, they were happy to welcome the group of their colleague Professor Didier Dubreuil in this structure.

 

1986: Ph.D. in organic chemistry under the direction of Prof. Eric BROWN at the University of Paris XI (France).

1986/87:  Postdoctoral fellow with Prof. James A. MARSHALL at the University of South Carolina.

1988/89: Postdoctoral fellow with Prof. Robert E. IRELAND at the University of Virginia.

1989/94: Senior scientist at CIBA-GEIGY AG (Basel, Switzerland).

1994/98: CNRS researcher (Marseille and Nantes, France).

1998: Full Professor at the University of Nantes (France).

Activity indicators: about 115 publications and patents (h-index 25)

Recent publications and patents

I. CHATAIGNER, F. ZAMMATTIO, J. LEBRETON, J. VILLIÉRAS. Enantioselective addition of b-functionalized allylboronates to aldehydes and aldimines. Stereocontrolled synthesis of alpha-methylene-gama-lactones and lactams. Tetrahedron, 64, 2441-2455, 2008.

 C. LEN, M. MONDON, J. LEBRETON. Synthesis of cyclonucleosides having a C-C bridge. Tetrahedron, 64, 7453-7475, 2008.

 W. HATTON, V. SILVESTRE, R. J. ROBINS, M. MATHE-ALLAINMAT, J. LEBRETON. Synthesis of four racemic nicotine isotopomers doubly-labelled with stable isotope. Labelled Compounds and radiopharmaceuticals, 2009, 52, 117-122.

 M. EGOROV, Y. FORTUN, D. HEYMANN, J. LEBRETON, M. MATHE-ALLAINMAT, M. PADRINES, F. REDINI. Improved process for preparation of 1-hydroxy-1,1-diphosphonic acids and salts by addition of tris(trimethylsilyl) phosphite to carboxylic acids, activated by catecholboran. International patent, WO 2009083613 A1 20090709 (2009) licensed to Atlantic Bone Screen.

 M. EGOROV, Y. FORTUN, D. HEYMANN, J. LEBRETON, M. MATHE-ALLAINMAT, M. PADRINES, F. REDINI. Hydroxy-bisphosphonic acid derivatives as vectors for therapeutic and diagnostic targeting of bone tissue. International patent, WO 2009083614 A1 20090709 (2009) licensed to Atlantic Bone Screen.

 V. ARNAUD, M. BERTHELOT, F-X. FELPIN, J. LEBRETON, J.-Y. LEQUESTEL, J. GRATON. Hydrogen-Bond Accepting Strength of Five-Membered N-Heterocycles: The Case of Substituted Phenylpyrrolines and Myosmines. Eur. J. Org. Chem. 2009, 4939-4948.

 V. FARGEAS, A. ANE, D. DUBREUIL, J. LEBRETON. Synthesis of Carbon E,E-Diene Chain-Linked Dinucleotide Analogues. Synlett., 2009, 3341-3345.

A. BOUSSONNIERE, F. DENES, J. LEBRETON. Radical Cyclization of alpha-Bromo Aluminum Acetals: An Easy Approach to gama-Lactols. Angew. Chem. Int. Ed., 2009, 48, 9549-9552.

 A. FOURNIAL, T. RANAIVONDRAMBOLA, M. MATHE-ALLAINMAT, R. ROBINS, J. LEBRETON. A Short and Efficient Synthesis of Bridgehead Mono- and Dideuteriated Tropinones. Eur. J. Org. Chem., 2010, 152-156.

 J. LEBRETON, L.ARZEL, J.-M. ESCUDIER, C. LEN. Synthesis of Cyclonucleosides Having a C-C Bridge. Chem. Rev., cr-2008-00465j, accepted 02/10/2010.

Advisory board of European Journal of Organic Chemistry and Current Organic Synthesis.

Co-founder of Atlanchimpharma Laboratory (www.atlanchimpharma.com) (Custom-made fine chemicals and synthesis of labelled molecules with stable isotopes)

In 2001, he has received an award from Glaxo Smith Kline for the synthesis of a new family of inhibitors of the viral protein TAT (VIH) in a project directed by Erwan Loret (Marseille Centre for National Scientific Research).