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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Bibliographic Details
Published in:Tetrahedron 2012-04, Vol.68 (15), p.3210-3219
Main Authors: Urabe, Daisuke, Todoroki, Hidenori, Masuda, Koji, Inoue, Masayuki
Format: Article
Language:English
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
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Summary: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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2012.02.045