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A modular, enantioselective synthesis of resolvins D3, E1, and hybrids

DOI: 10.1021/acs.orglett.0c00089 DOI Help

Authors: Felix Urbitsch (Chemistry Research Laboratory, University of Oxford) , Bryony L. Elbert (Chemistry Research Laboratory, University of Oxford) , Josep Llaveria (UCB Pharma, Ltd) , Penelope E. Streatfeild (Chemistry Research Laboratory, University of Oxford) , Edward A. Anderson (Chemistry Research Laboratory, University of Oxford)
Co-authored by industrial partner: Yes

Type: Journal Paper
Journal: Organic Letters

State: Published (Approved)
Published: February 2020

Abstract: 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.

Journal Keywords: Alcohols; Anions; Siloxanes; Cross coupling reaction; Pharmaceuticals

Subject Areas: Chemistry

Technical Areas: