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

ID: ALA3351367

Journal: Bioorg Med Chem Lett

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

Authors: Gore V, Chourey S, Ye Q, Patel P, Ouedraogo Y, Gravel S, Powell WS, Rokach J.

Abstract: 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.

CiteXplore: 24948567

DOI: 10.1016/j.bmcl.2014.05.090

Patent ID: ┄