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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.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02385502
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Submitted on : Thursday, November 28, 2019 - 6:43:47 PM
Last modification on : Tuesday, September 22, 2020 - 3:38:23 AM

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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, Elsevier, 1995, 6 (8), pp.1989-1994. ⟨10.1016/0957-4166(95)00258-Q⟩. ⟨hal-02385502⟩

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