Synthesis of (3S,4S)-4-Hydroxy-2,3,4,5-Tetrahydropyridazine-3-Carboxylic Acid, Component of Luzopeptin A.

Article abstract of DOI:10.1016/0957-4166(95)00258-Q

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.