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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...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
2019
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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. |
format | Online Article Text |
id | pubmed-7709930 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
record_format | MEDLINE/PubMed |
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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