A focus on the asymmetric synthesis of a novel threo-ß-benzyl-ß-hydroxy aspartate analogue

Sofiane Mekki (1, 2) , Salima Bellahouel (1) , Nicolas Vanthuyne (3) , Marc Rolland (4) , Aïcha Derdour (1) , Jean Martinez (2) , Michel Vignes (2) , Valérie Rolland (2)

1 Laboratoire de Synthèse Organique Appliquée
2 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]
3 ISM2 - Institut des Sciences Moléculaires de Marseille
4 IEM - Institut Européen des membranes

Considering the biological activity of b-alkyl-b-hydroxyaspartate derivatives as potent blockers of glutamate transporters (EAATs) impacting on glutamatergic synapses activity, we have developed a concise, asymmetric synthesis of enantiomerically pure threo-b-benzyl-b-hydroxyaspartates. The key step is a regiospecific and stereoselective Sharpless asymmetric aminohydroxylation (SAA) on previously synthesized benzyl fumarate.

Domaines: Chimie organique

Sofiane Mekki, Salima Bellahouel, Nicolas Vanthuyne, Marc Rolland, Aïcha Derdour, et al.. A focus on the asymmetric synthesis of a novel threo-ß-benzyl-ß-hydroxy aspartate analogue. Tetrahedron: Asymmetry, 2012, 23, pp.94-99. ⟨10.1016/j.tetasy.2012.01.004⟩. ⟨hal-00668879⟩