Accueil > Publications > Recherche par années > Années 1990 > 1993

Alazard, JP ; Boye, O ; Gillet, B ; Guenard, D ; Beloeil, JC ; Thal, C

Compounds interacting with tubulin .1. Synthesis of ortho-ortho’ substituted phenylpyrroles with free or restricted rotation

Bulletin de la Societe Chimique de France 130 (6) 779-787

par Administrateur - publié le

Abstract :

The synthesis of ortho-ortho’ substituted phenylpyrroles that are susceptible to isomerization of the biaryl type (atropisomerism) was performed using a Michael addition of isocyanoacetates with nitrostyrenes. Atropisomerism in phenylpyrroles 14 and 15 was studied by means of H-1 NMR spectroscopy using chiral lanthanide shift reagents (LSR*). In the case of chiral phenylpyrrole 21, an evaluation of the interconversion parameters between diastereomers (k, ?G(T)*) was attempted.