Stereoselective synthesis of MaR2(n-3 DPA)

The first total synthesis of the n-3 docosapentaenoic derived oxygenated product MaR2(n-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...

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Detalles Bibliográficos
Autores principales: Sønderskov, Jeanne, Tungen, Jørn E., Palmas, Francesco, Dalli, Jesmond, Serhan, Charles N., Stenstrøm, Yngve, Hansen, Trond Vidar
Formato: Online Artículo Texto
Lenguaje:English
Publicado: 2019
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7709930/
https://www.ncbi.nlm.nih.gov/pubmed/33273748
http://dx.doi.org/10.1016/j.tetlet.2019.151510
Descripción
Sumario:The first total synthesis of the n-3 docosapentaenoic derived oxygenated product MaR2(n-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 MaR2(n-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.

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