First total synthesis of the anti-inflammatory lipid mediator Resolvin D6

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• 作者：Ana R. Rodriguez ; Bernd W. Spur  ; ;   ; ^{spurbw@umdnj.edu}
• 关键词：Resolvin D6 ; Total synthesis ; Inflammation resolution ; Asymmetric transfer hydrogenation ; Asymmetric epoxidation
• 刊名：Tetrahedron Letters
• 出版年：2012
• 出版时间：4 January 2012
• 年：2012
• 卷：53
• 期：1
• 页码：86-89
• 全文大小：208 K

文摘

The first total synthesis of Resolvin D6, an endogenous lipid mediator of resolution of inflammation derived from docosahexaenoic acid, has been achieved. The chiral hydroxy-groups at C4 and C17 were generated via an asymmetric Noyori transfer hydrogenation and a Sharpless catalytic asymmetric epoxidation, respectively. A mild copper catalyzed coupling of cis-1,4-dibromo-2-butene with TMS-acetylene generated the C7¨CC14 fragment. Pd⁰/Cu^I Sonogashira couplings and Zn(Cu/Ag) reduction completed the synthesis of Resolvin D6.