Université de Fribourg

Phytotoxic metabolites from Neofusicoccum parvum, a pathogen of Botryosphaeria dieback of grapevine

Abou-Mansour, Eliane ; Débieux, Jean-Luc ; Ramírez-Suero, Montserrat ; Bénard-Gellon, Mélanie ; Magnin-Robert, Maryline ; Spagnolo, Alessandro ; Chong, Julie ; Farine, Sibylle ; Bertsch, Christohpe ; L’Haridon, Floriane ; Serrano, Mario ; Fontaine, Florence ; Rego, Cecilia ; Larignon, Philippe

In: Phytochemistry, 2015, vol. 115, p. 207–215

Liquid chromatography-diode array screening of the organic extract of the cultures of 13 isolates of the fungus Neofusicoccum parvum, the main causal agent of botryosphaeria dieback of grapevine, showed similar metabolites. One strain was selected for further chemical studies and led to the isolation and characterisation of 13 metabolites. Structures were elucidated through spectroscopic...

Université de Fribourg

Synthesis of Hexa-peri-hexobenzocoronenes Carrying Linear or Branched Perfluoroalkylated Side Chains

Aebischer, Olivier F. ; Muñoz, David T. ; Tondo, Patrick ; Débieux, Jean-Luc ; Jenny, Titus A.

In: Synthesis, 2010, vol. 7, p. 1123-1140

Substituted disc-shaped perfluoroalkylated hexa-peri-hexabenzocoronenes (HBC), known to self-assemble into conducting ordered architectures, were synthesized and characterized. A systematic variation of the linear or branched perfluoroalkylated side chains was performed in order to screen the influence of the lateral chain on their one-dimensional self-aggregation.

Université de Fribourg

Photoinduced acyl transfer

Débieux, Jean-Luc ; Bochet, Christian G.

In: Journal of Physical Organic Chemistry, 2010, p. -

The acylation reaction occupies a central role in biochemistry and organic synthesis. On the one hand, it is by this very reaction that amino acids successively assemble to form peptides and proteins, and on the other hand it is a major synthetic method encompassing esterification, amidation, Friedel-Crafts reaction and many other processes routinely used both at the laboratory and the industrial...

Université de Fribourg

Preparation of photoactivable amino acid derivatives

Débieux, Jean-Luc ; Bochet, Christian G.

In: Journal of Organic Chemistry, 2009, vol. 74, no. 12, p. 4519–4524

A range of N-protected-α-amino acyl-5,7-dinitroindolines 3a−z were prepared in good yields from commercially available N-protected-α-amino acids 1a−z by a two-step sequence of acylation and intramolecular amide N-arylation. Subsequent photochemical acylation of the N-protected-α-amino acyl-5,7-dinitroindolines 3e,g,r afforded the corresponding N-protected-α-amino acid amides 22e,g,r...

Université de Fribourg

Photoacylation of alcohols in neutral medium

Débieux, Jean-Luc ; Cosandey, Anne ; Helgen, Céline ; Bochet, Christian G.

In: European Journal of Organic Chemistry, 2007, p. 2073 - 2077

We report here conditions which allow the photoacylation of primary, secondary and tertiary alcohols with N-acetyl-5,7-dinitroindoline under exceptionally mild conditions, at wavelengths harmless to most functional groups, including otherwise photosensitive ones.