Synthesis of (3S, 4S)-4-hydroxy-2, 3, 4, 5-tetrahydropyridazine-3-carboxylic acid, component of luzopeptin A.

Christine Greck (1) , Laurent Bischoff (2) , Jean Pierre Genêt (3)

1 ILV - Institut Lavoisier de Versailles
2 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
3 ENSCP - Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL

The enantioselective synthesis of (3S, 4S)-4-hydroxy-2, 3, 4, 5-tetrahydropyridazine-3-carboxylic acid 1 is described. The two stereogenic centers in anti relationship are obtained by sequential enantio and chemoselective hydrogenation of β-ketoester in presence of chiral ruthenium catalyst and diastereoselective amination of β-hydroxyester with di t-butylazodicarboxylate.

Domains: Chemical Sciences; Chemical Sciences; Organic chemistry; Chemical Sciences; Medicinal Chemistry; Chemical Sciences; Radiochemistry; Chemical Sciences; Material chemistry; Chemical Sciences; Inorganic chemistry; Chemical Sciences; Catalysis

Christine Greck, Laurent Bischoff, Jean Pierre Genêt. Synthesis of (3S, 4S)-4-hydroxy-2, 3, 4, 5-tetrahydropyridazine-3-carboxylic acid, component of luzopeptin A.. Tetrahedron: Asymmetry, 1995, 6 (8), pp.1989-1994. ⟨10.1016/0957-4166(95)00258-Q⟩. ⟨hal-02385502⟩