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Jean-Pierre HURVOIS

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Jean-Pierre HURVOIS

UR1 Full Professor

HURVOIS Jean-Pierre – UR1 – Full Professor
Université de Rennes 1
Faculté des Sciences Pharmaceutiques et Biologiques
Pharmacie : Institut des sciences chimiques de Rennes - UMR 6226
2 - Av du Pr. Léon Bernard - CS 34317 - 35043 - RENNES CEDEX
Building 05-East, Office 00-034
Phone: +33 (0) 2.23.23.65.48
Email: jean-pierre.hurvois@univ-rennes1.fr

Research Themes

• Total Synthesis of piperidine and isoquinoline alkaloids.
see Electrochemistry

Key Words / Scientiofic Skills

• Stereoselective synthesis, a-amino nitriles
• Anodic Cyanation/Electrochemical C-H activation.
• Pyridinium salts dearomatization.
• Cyclic Voltamperometry.

Education and professional experience

• Actual position (Full Professor in Chemistry).
• post-doctoral fellow (2002 – 2003, Université Paris Descartes).
• PhD (1990/1993, Rennes).
• Faculty of Pharmacy (1980-1985, Rennes).

Teaching activities

• General and molecular electrochemistry.
• Molecular Pharmacology.

Scientific Production

Summary

Electrosynthesis of alkaloids
Piperidine and isoquinoline derivatives form a large group of substance that are found in Nature and Pharmacenticals. Their biological properties prompted chemist to discover new synthetic tools aimed at the elaboration of new carbon to carbon bonds in the position  to the nitrogen atom. In this regard, the alkylation-decyanation sequence of new a-amino nitrile systems constitutes an efficient mean to achieve this goal and to control the absolute configuration of the newly created stereogenic center. In addition, the electrochemical synthesis of -amino nitriles has been little studied to date.
With this purpose in mind, new a-amino nitriles were elaborated through the anodic cyanation of conveniently substituted nitrogen containing derivatives such as N-aryl-piperidines, N-alkyl-isoquinolines and N-alkyl-quinolines. We were able to demonstrate that the introduction of the cyano substituent can be achieved in a regio- and stereoselective manner. In addition, the -proton can be removed efficiently with a strong base such as LDA to produce an -amino carbanion which can be condensed on a large variety of electrophiles. This strategy allowed the racemic syntheses of several major alkaloids such as coniine, solenopsin A, pumiliotoxin-C, alkaloid 241D, angustureine and galipinine (Figure 1).

Similarly, (+)-myrtine, (–)-crispine and (–)-xylopinine were synthesized in both enantiomeric forms utilizing (+) and (–)--phenylethylamine as a source of nitrogen and chirality (Figure 2).

• Total synthesis of (±)-pumiliotoxin C: An electrochemical approach, N. Girard, J. P. Hurvois, C. Moinet, L. Toupet, Eur. J. Org. Chem, 2005, 2269–2280.

• Synthesis of tetrahydroisoquinoline alkaloids via anodic cyanation as key step. F. Louafi, J.-P. Hurvois, A. Chibani, T. Roisnel, J. Org. Chem. 2010, 5721–5724.

• Electrochemical Synthesis and Chemistry of Chiral 1-Cyanotetrahydroisoquinolines. An approach to the Asymmetric Syntheses of the Alkaloid (–)-crispine A and its Natural (+)-Antipode. F. Louafi, J. Moreau, S. Shahane, S. Golhen, T. Roisnel, S. Sinbandhit, J. P. Hurvois J. Org. Chem. 2011, 9720–9732.

• Electrochemical Access to 8-(1-Phenyl-ethyl)-1,4-dioxa-8-aza-spiro[4.5]decane-7-carbonitrile. Application to the Asymmetric Syntheses of (+)-Myrtine and Alkaloid (+)-241D. V. H. Vu, F. Louafi, N. Girard, R. Marion, T. Roisnel, V. Dorcet, J.-P. Hurvois. J. Org. Chem. 2014, 79, 3358–3373.

• Synthesis of Tetrahydroisoquinoline Alkaloids and Related Compounds through the Alkylation of Anodically Prepared -Amino Nitriles. L. Benmekhbi, F. Louafi, T. Roisnel, J.-P. Hurvois. J. Org. Chem. 2016, 81, 6721.

Publications referenced in HAL