title: Base-dependent formation of cis and trans olefins and their application in the synthesis of 5-oxo-ETE receptor antagonists.
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.
authors.affiliation: Claude Pepper Institute and Department of Chemistry, Florida Institute of Technology, 150 West University Boulevard, Melbourne, FL 32901, USA.
authors.forename: Vivek
authors.initials: V
authors.lastname: Gore
authors.affiliation: Claude Pepper Institute and Department of Chemistry, Florida Institute of Technology, 150 West University Boulevard, Melbourne, FL 32901, USA.
authors.forename: Shishir
authors.initials: S
authors.lastname: Chourey
authors.affiliation: Claude Pepper Institute and Department of Chemistry, Florida Institute of Technology, 150 West University Boulevard, Melbourne, FL 32901, USA.
authors.forename: Qiuji
authors.initials: Q
authors.lastname: Ye
authors.affiliation: Claude Pepper Institute and Department of Chemistry, Florida Institute of Technology, 150 West University Boulevard, Melbourne, FL 32901, USA.
authors.forename: Pranav
authors.initials: P
authors.lastname: Patel
authors.affiliation: Claude Pepper Institute and Department of Chemistry, Florida Institute of Technology, 150 West University Boulevard, Melbourne, FL 32901, USA.
authors.forename: Yannick
authors.initials: Y
authors.lastname: Ouedraogo
authors.affiliation: Meakins-Christie Laboratories, Department of Medicine, McGill University, Montreal, Quebec H2X 2P2, Canada.
authors.forename: Sylvie
authors.initials: S
authors.lastname: Gravel
authors.affiliation: Meakins-Christie Laboratories, Department of Medicine, McGill University, Montreal, Quebec H2X 2P2, Canada.
authors.forename: William S
authors.initials: WS
authors.lastname: Powell
authors.affiliation: Claude Pepper Institute and Department of Chemistry, Florida Institute of Technology, 150 West University Boulevard, Melbourne, FL 32901, USA. Electronic address: jrokach@fit.edu.
authors.forename: Joshua
authors.initials: J
authors.lastname: Rokach
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D018055:Receptors, Eicosanoid / Q000037:antagonists & inhibitors*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000475:Alkenes; D018055:Receptors, Eicosanoid
keywords: 5-Oxo-ETE; Antagonist; Indolecarboxaldehyde; KHMDS; LiHMDS; Wittig reaction