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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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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:
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
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author Sønderskov, Jeanne
Tungen, Jørn E.
Palmas, Francesco
Dalli, Jesmond
Serhan, Charles N.
Stenstrøm, Yngve
Hansen, Trond Vidar
author_facet Sønderskov, Jeanne
Tungen, Jørn E.
Palmas, Francesco
Dalli, Jesmond
Serhan, Charles N.
Stenstrøm, Yngve
Hansen, Trond Vidar
author_sort Sønderskov, Jeanne
collection PubMed
description 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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spelling pubmed-77099302020-12-02 Stereoselective synthesis of MaR2(n-3 DPA) Sønderskov, Jeanne Tungen, Jørn E. Palmas, Francesco Dalli, Jesmond Serhan, Charles N. Stenstrøm, Yngve Hansen, Trond Vidar Tetrahedron Lett Article 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. 2019-12-09 2020-02-13 /pmc/articles/PMC7709930/ /pubmed/33273748 http://dx.doi.org/10.1016/j.tetlet.2019.151510 Text en This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Article
Sønderskov, Jeanne
Tungen, Jørn E.
Palmas, Francesco
Dalli, Jesmond
Serhan, Charles N.
Stenstrøm, Yngve
Hansen, Trond Vidar
Stereoselective synthesis of MaR2(n-3 DPA)
title Stereoselective synthesis of MaR2(n-3 DPA)
title_full Stereoselective synthesis of MaR2(n-3 DPA)
title_fullStr Stereoselective synthesis of MaR2(n-3 DPA)
title_full_unstemmed Stereoselective synthesis of MaR2(n-3 DPA)
title_short Stereoselective synthesis of MaR2(n-3 DPA)
title_sort stereoselective synthesis of mar2(n-3 dpa)
topic Article
url 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
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