Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5219701 | Tetrahedron | 2012 | 10 Pages |
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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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Daisuke Urabe, Hidenori Todoroki, Koji Masuda, Masayuki Inoue,