手性选择性合成 7()-羟基二十二碳六烯酸，一种可能的 PPARα 内源性配体。
Enantioselective Synthesis of 7()-Hydroxydocosahexaenoic Acid, a Possible Endogenous Ligand for PPARα.
机构信息
Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario M3J 1P3, Canada.
出版信息
J Org Chem. 2020 Nov 6;85(21):13621-13629. doi: 10.1021/acs.joc.0c01770. Epub 2020 Oct 15.
We report the first total synthesis of the polyunsaturated fatty acid 7-hydroxydocosahexaenoic acid (7-HDHA) in racemic form and the enantioselective synthesis of 7-()-HDHA. Both syntheses follow a convergent approach that unites the C1-C9 and C10-C22 fragments using Sonogashira coupling and Boland reduction as key steps. These syntheses enabled the unambiguous characterization of this natural product for the first time and helped establish 7()-HDHA as a possible endogenous ligand for peroxisome proliferator-activated receptor alpha.
我们报告了全反式 7-羟基二十二碳六烯酸（7-HDHA）的首次立体选择性全合成，该化合物以 rac 形式存在。两种合成方法均采用了汇聚策略，通过 Sonogashira 偶联和 Boland 还原作为关键步骤，将 C1-C9 和 C10-C22 片段连接起来。这些合成方法首次使该天然产物的特征得以明确，并有助于确定 7-()-HDHA 可能是过氧化物酶体增殖物激活受体α的内源性配体。
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