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

Christine Greck; Laurent Bischoff; Jean Pierre Genêt

doi:10.1016/0957-4166(95)00258-Q

Journal articles

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

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.

Document type :

Journal articles

Domain :

Chemical Sciences

Chemical Sciences / Organic chemistry

Chemical Sciences / Medicinal Chemistry

Chemical Sciences / Radiochemistry

Chemical Sciences / Material chemistry

Chemical Sciences / Inorganic chemistry

Chemical Sciences / Catalysis

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

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

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

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