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

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 contr...

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Bibliographic Details
Published inOrganic letters Vol. 22; no. 4; pp. 1510 - 1515
Main Authors Urbitsch, Felix, Elbert, Bryony L, Llaveria, Josep, Streatfeild, Penelope E, Anderson, Edward A
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.02.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Letter
Physical Sciences
Science & Technology
CROSS-COUPLING REACTIONS
GENERAL-SYNTHESIS
REDUCTION
KINETIC RESOLUTION
INFLAMMATION
1ST TOTAL-SYNTHESIS
STEREOSELECTIVE-SYNTHESIS
LIPID MEDIATORS
EPOXIDATION
MEDIUM-SIZED RINGS
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c00089