Université de Neuchâtel

Malonylation/Decarbalkoxylation of Furan Derivatives as Key Steps for the Preparation of Nonactic Acid Derivatives. Part I [1]

Simone, Jean-Mary ; Loiseau, François ; Carcache, David ; Bobal, Pavel ; Jeanneret-Gris, Julie ; Neier, Reinhard

In: Monatshefte für Chemie / Chemical Monthly, 2007, vol. 138, no. 2, p. 131-139

A malonylation/decarbalkoxylation sequence from 2-substituted furans was investigated in view of developing a scalable synthesis of hydrophobic nonactic acid analogues.

Université de Neuchâtel

Radical Couplings as Key Steps for the Preparation of Derivatives of Nonactic Acid

Loiseau, François ; Simone, Jean-Mary ; Carcache, David ; Bobal, Pavel ; Neier, Reinhard

In: Monatshefte für Chemie / Chemical Monthly, 2007, vol. 138, no. 2, p. 121-129

Free radical couplings from furan, as cheap starting material, were studied in view of developing a rapid strategy en route to the synthesis of derivatives of nonactin. The chain containing the alcohol function was introduced in one or two steps in 86% yield. For the introduction of the second chain with the ester function two different coupling methods were tested. Starting from the...

Université de Neuchâtel

Macrocyclisation of 2-(5-(2-hydroxyethyl)furan-2-yl)acetic acid model compounds of nonactic acid

Eng, Carine ; Simone, Jean-Mary ; Hartenbach, Akane ; Loiseau, François ; Neier, Reinhard

In: Monatshefte für Chemie / Chemical Monthly, 2009, vol. 140, no. 3, p. 349-354

The macrocyclisation of hydroxyethylfuranyl acetic acid and of dehydrogenated model compounds of nonactic acid was investigated to develop a facile synthesis of nonactin analogues. By applying the Yamagushi macrocyclisation to our ω-hydroxyacids, we were able to isolate a mixture of di-, tri-, tetra- and pentameric macrocycles.

Université de Neuchâtel

rac-Ethyl 2-bromo-2-[(3R,5R)-3-bromo-5-methyltetrahydrofuran-2-ylidene]acetate

Loiseau, François ; Neier, Reinhard ; Labat, Gael ; Stoeckli-Evans, Helen

In: Acta Crystallographica Section C, 2006, vol. 62, no. 11, p. o636-o638

In the title compound, C9H12Br2O3, a (tetrahydrofuran-2-ylidene)acetate, the double bond has the Z form. In the tetrahydrofuran group, the relative configuration of the Br atom in the 3-position and the methyl group in the 5-position is anti. The compound crystallizes with two independent molecules per asymmetric unit and, in the crystal...

Université de Neuchâtel

rac-(R)-2-[(2R,5R)-5-Methyl­tetra­hydro­furan-2-yl]propanoic acid

Loiseau, François ; Neier, Reinhard ; Stoeckli-Evans, Helen

In: Acta Crystallographica Section E, 2006, vol. E, no. 62, p. o3407-o3409

In the crystal structure of the title compound, C8H14O3, the 2,5-tetra­hydro­furan ring junction is cis. The relative configuration of position 2 in the propanoic acid group was found to be the same as that in positions 2 and 5 in the tetra­hydro­furan ring. In the crystal structure, symmetry-related mol­ecules are linked by O***HO hydrogen bonds to form...

Université de Neuchâtel

Malonylation/Decarbalkoxylation of Furan Derivatives as Key Steps for the Preparation of Nonactic Acid Derivatives. Part II [1]

Simone, Jean-Mary ; Loiseau, François ; Carcache, David ; Bobal, Pavel ; Jeanneret-Gris, Julie ; Neier, Reinhard

In: Monatshefte für Chemie / Chemical Monthly, 2007, vol. 138, no. 2, p. 141-147

A malonylation/decarbalkoxylation sequence from 2-substituted furans was investigated in view of developing a scalable synthesis of hydrophobic nonactic acid analogues.