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Total syntheses of four possible stereoisomers of resolvin E3
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...
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| Published in: | Tetrahedron 2012-04, Vol.68 (15), p.3210-3219 |
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| Main Authors: | , , , |
| Format: | Article |
| Language: | English |
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| cites | cdi_FETCH-LOGICAL-c426t-8b0abd27564d52d2c1cc242c8fb28abf0d8c70e187be764f44e25c300e504e6f3 |
| container_end_page | 3219 |
| container_issue | 15 |
| container_start_page | 3210 |
| container_title | Tetrahedron |
| container_volume | 68 |
| creator | Urabe, Daisuke Todoroki, Hidenori Masuda, Koji Inoue, Masayuki |
| description | 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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| doi_str_mv | 10.1016/j.tet.2012.02.045 |
| format | article |
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| ispartof | Tetrahedron, 2012-04, Vol.68 (15), p.3210-3219 |
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| language | eng |
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| source | ScienceDirect Freedom Collection |
| subjects | Alkynes Biological Biological and medical sciences Bones, joints and connective tissue. Antiinflammatory agents Chemistry Convergent strategy Eicosapentaenoic acid Exact sciences and technology Joining Lipid mediators Lipids Medical sciences Organic chemistry Pharmacology. Drug treatments Preparations and properties Reduction Resolvin Stereochemistry Tetrahedrons Total synthesis |
| title | Total syntheses of four possible stereoisomers of resolvin E3 |
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