Base-dependent formation of cis and trans olefins and their application in the synthesis of 5-oxo-ETE receptor antagonists

Base-dependent formation of cis and trans olefins and their application in the synthesis of 5-oxo-ETE receptor antagonists

5-Oxo-ETE is the most potent eosinophil chemoattractant among lipid mediators. We have developed two 5-oxo-ETE receptor antagonists. In the course of the work, we have developed a procedure to selectively introduce a cis and trans double bond in an alkyl side chain. Reacting indolecarboxaldehydes wi...

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Veröffentlicht in:Bioorganic & medicinal chemistry letters 2014-08, Vol.24 (15), p.3385-3388
Hauptverfasser: Gore, Vivek, Chourey, Shishir, Ye, Qiuji, Patel, Pranav, Ouedraogo, Yannick, Gravel, Sylvie, Powell, William S, Rokach, Joshua
Format: Artikel
Sprache:eng
Schlagworte:
Alkenes - chemical synthesis
Alkenes - chemistry
Alkenes - pharmacology
Molecular Structure
Receptors, Eicosanoid - antagonists & inhibitors
Stereoisomerism
Structure-Activity Relationship
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Zusammenfassung:5-Oxo-ETE is the most potent eosinophil chemoattractant among lipid mediators. We have developed two 5-oxo-ETE receptor antagonists. In the course of the work, we have developed a procedure to selectively introduce a cis and trans double bond in an alkyl side chain. Reacting indolecarboxaldehydes with alkyl ylides using the Li base affords the trans olefins, whereas using the K base yields the cis olefins.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2014.05.090