Total syntheses of four possible stereoisomers of resolvin E3 |
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Authors: | Daisuke Urabe Hidenori Todoroki Koji Masuda Masayuki Inoue |
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Institution: | 1. Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan;2. Shionogi & Co. Ltd., Discovery Research Laboratories, Sagisu, Fukushima-ku, Osaka 541-0045, Japan |
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Abstract: | 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. |
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