Total syntheses of four possible stereoisomers of resolvin E3
Total syntheses of four possible stereoisomers of resolvin E3
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DOI：
10.1016/j.tet.2012.02.045
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发表时间：
2012-04-15
期刊：
影响因子：
2.1
通讯作者：
Inoue, Masayuki
中科院分区：
文献类型：
--
作者：
Urabe, Daisuke;Todoroki, Hidenori;Inoue, Masayuki
分解酶E3，17，18-dihydroxy-5Z，8Z，11Z，13E，15E-eicosapentaenoic酸，是一种有效的抗炎脂质介体。为了确定拆分蛋白E3的C17-和C18-羟基的立体化学，并为未来的生物学研究提供足够的材料，我们开发了一条高度收敛和实用的路线来合成它的四个可能的立体异构体。其中的关键反应是Horner-Wadsworth-Emmons偶联反应，两个铜(I)介导的炔烃和炔丙基对甲苯磺酸盐之间的反应，以及三个三键同时还原为三个Z-烯烃。(C)2012爱思唯尔有限公司。保留所有权利。
Resolvin E3, 17,18-dihydroxy-5Z,8Z,11Z,13E,15E-eicosapentaenoic acid, is a potent anti-inflammatory lipid mediator. To determine the stereochemistries of the C17- and C18-hydroxy groups of resolvin E3 and to supply a sufficient amount of material for future biological studies, we developed a highly convergent and practical route to its four possible stereoisomers. The key reactions employed here were the Horner-Wadsworth-Emmons coupling, the two copper(I)-mediated reactions between the alkynes and the propargyl tosylates, and the simultaneous reduction of the three triple bonds to the three Z-olefins. (C) 2012 Elsevier Ltd. All rights reserved.