Synthesis of (3S, 4S)-4-hydroxy-2, 3, 4, 5-tetrahydropyridazine-3-carboxylic acid, component of luzopeptin A. - Archive ouverte HAL Access content directly
Journal Articles Tetrahedron: Asymmetry Year : 1995

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

Abstract

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.

Dates and versions

hal-02385502 , version 1 (28-11-2019)

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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⟩
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