Stereoselective synthesis of MaR2n-3 DPA
| Autor: | Francesco Palmas, Yngve Stenstrøm, Trond Vidar Hansen, Jeanne Sønderskov, Jørn Eivind Tungen, Charles N. Serhan, Jesmond Dalli |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2019 |
| Předmět: |
Natural product
n-3 docosapentaenoic acid 010405 organic chemistry Stereochemistry Organic Chemistry Specialized pro-resolving mediator Total synthesis 010402 general chemistry 01 natural sciences Biochemistry Article 0104 chemical sciences Stereocenter chemistry.chemical_compound chemistry Product (mathematics) Drug Discovery Wittig reaction Moiety Stereoselectivity MaR2n-3 DPA Maresins |
| Zdroj: | Tetrahedron letters |
| ISSN: | 0040-4039 |
| Popis: | The first total synthesis of the n-3 docosapentaenoic derived oxygenated product MaR2n-3 DPA has been achieved. The 13R and 14S stereogenic centers were introduced using 2-deoxy-d-ribose in a chiral pool strategy. The geometry of the Z,E,E-triene moiety was prepared using highly E-selective Wittig- and Takai-olefination reactions as well as the Z-stereoselective Lindlar reduction. LC/MS-MS data of synthetic MaR2n-3 DPA matched data for the biosynthetic formed product that enabled the configurational assignment of this oxygenated natural product to be (7Z,9E,11E,13R,14S,16Z,19Z)-13,14-dihydroxydocosa-7,9,11,16,19-pentaenoic acid. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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