Stereocontrolled Synthesis of (−)-Kainic Acid from trans-4-Hydroxy-l-proline

Stereocontrolled Synthesis of (−)-Kainic Acid from trans-4-Hydroxy-l-proline

A highly stereoselective synthesis of (−)-kainic acid has been achieved in 14 steps and >7% overall yield starting from inexpensive trans-4-hydroxy-l-proline. The key steps are diastereoselective enolate alkylation and cuprate substitution reactions.

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Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2005-12, Vol.70 (26), p.10860-10863
Hauptverfasser: Poisson, Jean-François, Orellana, Arturo, Greene, Andrew E
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
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Beschreibung
Zusammenfassung:A highly stereoselective synthesis of (−)-kainic acid has been achieved in 14 steps and >7% overall yield starting from inexpensive trans-4-hydroxy-l-proline. The key steps are diastereoselective enolate alkylation and cuprate substitution reactions.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo051508t