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
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Alkenes - chemical synthesis
Alkenes - chemistry
Alkenes - pharmacology
Molecular Structure
Receptors, Eicosanoid - antagonists & inhibitors
Stereoisomerism
Structure-Activity Relationship
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container_end_page 3388
container_issue 15
container_start_page 3385
container_title Bioorganic & medicinal chemistry letters
container_volume 24
creator Gore, Vivek
Chourey, Shishir
Ye, Qiuji
Patel, Pranav
Ouedraogo, Yannick
Gravel, Sylvie
Powell, William S
Rokach, Joshua
description 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.
doi_str_mv 10.1016/j.bmcl.2014.05.090
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source MEDLINE; Elsevier ScienceDirect Journals
subjects Alkenes - chemical synthesis
Alkenes - chemistry
Alkenes - pharmacology
Molecular Structure
Receptors, Eicosanoid - antagonists & inhibitors
Stereoisomerism
Structure-Activity Relationship
title Base-dependent formation of cis and trans olefins and their application in the synthesis of 5-oxo-ETE receptor antagonists
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