A Modular, Enantioselective Synthesis of Resolvins D3, E1, and Hybrids

[Image: see text] Resolvins D3 and E1 are important signaling molecules in the resolution of inflammation. Here, we report a convergent and flexible strategy to prepare these natural products using Hiyama–Denmark coupling of five- and six-membered cyclic alkenylsiloxanes to connect three resolvin fr...

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Autores principales: Urbitsch, Felix, Elbert, Bryony L., Llaveria, Josep, Streatfeild, Penelope E., Anderson, Edward A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7146891/
https://www.ncbi.nlm.nih.gov/pubmed/32031820
http://dx.doi.org/10.1021/acs.orglett.0c00089
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author Urbitsch, Felix
Elbert, Bryony L.
Llaveria, Josep
Streatfeild, Penelope E.
Anderson, Edward A.
author_facet Urbitsch, Felix
Elbert, Bryony L.
Llaveria, Josep
Streatfeild, Penelope E.
Anderson, Edward A.
author_sort Urbitsch, Felix
collection PubMed
description [Image: see text] Resolvins D3 and E1 are important signaling molecules in the resolution of inflammation. Here, we report a convergent and flexible strategy to prepare these natural products using Hiyama–Denmark coupling of five- and six-membered cyclic alkenylsiloxanes to connect three resolvin fragments, and control the stereochemistry of the natural product (Z)-alkenes. The modular nature of this approach enables the synthesis of novel resolvin hybrids, opening up opportunities for more-extensive investigations of resolvin biology.
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spelling pubmed-71468912020-04-13 A Modular, Enantioselective Synthesis of Resolvins D3, E1, and Hybrids Urbitsch, Felix Elbert, Bryony L. Llaveria, Josep Streatfeild, Penelope E. Anderson, Edward A. Org Lett [Image: see text] Resolvins D3 and E1 are important signaling molecules in the resolution of inflammation. Here, we report a convergent and flexible strategy to prepare these natural products using Hiyama–Denmark coupling of five- and six-membered cyclic alkenylsiloxanes to connect three resolvin fragments, and control the stereochemistry of the natural product (Z)-alkenes. The modular nature of this approach enables the synthesis of novel resolvin hybrids, opening up opportunities for more-extensive investigations of resolvin biology. American Chemical Society 2020-02-07 2020-02-21 /pmc/articles/PMC7146891/ /pubmed/32031820 http://dx.doi.org/10.1021/acs.orglett.0c00089 Text en Copyright © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Urbitsch, Felix
Elbert, Bryony L.
Llaveria, Josep
Streatfeild, Penelope E.
Anderson, Edward A.
A Modular, Enantioselective Synthesis of Resolvins D3, E1, and Hybrids
title A Modular, Enantioselective Synthesis of Resolvins D3, E1, and Hybrids
title_full A Modular, Enantioselective Synthesis of Resolvins D3, E1, and Hybrids
title_fullStr A Modular, Enantioselective Synthesis of Resolvins D3, E1, and Hybrids
title_full_unstemmed A Modular, Enantioselective Synthesis of Resolvins D3, E1, and Hybrids
title_short A Modular, Enantioselective Synthesis of Resolvins D3, E1, and Hybrids
title_sort modular, enantioselective synthesis of resolvins d3, e1, and hybrids
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7146891/
https://www.ncbi.nlm.nih.gov/pubmed/32031820
http://dx.doi.org/10.1021/acs.orglett.0c00089
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