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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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Detalles Bibliográficos
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
Descripción
Sumario:[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.