Total synthesis of the anti-inflammatory lipid mediator Resolvin E2

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• 作者：Ana R. Rodriguez ; Bernd W. Spur ; ^{spurbw@umdnj.edu}
• 关键词：Resolvin E2 ; Total synthesis ; Inflammation resolution ; Asymmetric transfer hydrogenation in water ; Sonogashira coupling
• 刊名：Tetrahedron Letters
• 出版年：2012
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：11 April, 2012
• 卷：53
• 期：15
• 页码：1912-1915
• 文件大小：198 K

摘要

The total synthesis of Resolvin E2, an endogenous lipid mediator of the resolution of inflammation derived from eicosapentaenoic acid, has been achieved. The chiral hydroxy-groups at C5 and C18 were generated in a simple, efficient, and environmentally friendly manner via an asymmetric Noyori transfer hydrogenation in water using sodium formate as a reducing agent. Pd⁰/Cu^I Sonogashira couplings of the three key fragments and Zn(Cu/Ag) reduction completed the synthesis of Resolvin E2.