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

Vivek Gore Shishir Chourey Qiuji Ye Pranav Patel Yannick Ouedraogo Sylvie Gravel William S Powell Joshua Rokach

Bioorg Med Chem Lett

Claude Pepper Institute and Department of Chemistry, Florida Institute of Technology, 150 West University Boulevard, Melbourne, FL 32901, USA. Electronic address:

Published: August 2014

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.

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http://dx.doi.org/10.1016/j.bmcl.2014.05.090DOI Listing

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