期刊
TETRAHEDRON
卷 68, 期 15, 页码 3210-3219出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.02.045
关键词
Resolvin; Lipid mediators; Eicosapentaenoic acid; Total synthesis; Convergent strategy
资金
- JSPS
- Grants-in-Aid for Scientific Research [12J10348] Funding Source: KAKEN
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.
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