促消退脂质介质7（），12（），13（）-消退素T2及其13（）-差向异构体的首次全合成。
First total synthesis of the pro-resolving lipid mediator 7(),12(),13()-Resolvin T2 and its 13()-epimer.
作者信息
Rodriguez Ana R, Spur Bernd W
机构信息
Department of Cell Biology and Neuroscience, Rowan University-SOM, Stratford, NJ 08084, USA.
出版信息
Tetrahedron Lett. 2020 May 14;61(20). doi: 10.1016/j.tetlet.2020.151857. Epub 2020 Mar 19.
Abstract
The first total synthesis of the pro-resolving lipid mediator 7(),12(),13()-Resolvin T2 [7(), 12(), 13()-RvT2] and its 13()-epimer, derived from n-3 docosapentaenoic acid (n-3 DPA), are described. 7(), 12(), 13()-RvT2 and its 13()-epimer were obtained by total synthesis using a chiral pool strategy to introduce the chiral centers. C7 was generated from -(-)-1,2,4-butanetriol in both molecules and the C12 and C13 centers were generated from L-(+)-ribose and D-(-)-arabinose respectively. and -selective Wittig reactions, selective deprotections, and Dess-Martin periodinane oxidation were the key steps in the syntheses.
摘要
本文描述了源自n-3二十二碳五烯酸（n-3 DPA）的促消退脂质介质7(),12(),13()-Resolvin T2 [7(), 12(), 13()-RvT2]及其13()-差向异构体的首次全合成。7(), 12(), 13()-RvT2及其13()-差向异构体通过采用手性源策略引入手性中心的全合成方法获得。两个分子中的C7均由-(-)-1,2,4-丁三醇生成，C12和C13中心分别由L-(+)-核糖和D-(-)-阿拉伯糖生成。和-选择性维蒂希反应、选择性脱保护反应以及戴斯-马丁高碘烷氧化反应是合成中的关键步骤。
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