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

Felix Urbitsch | Zendy; Bryony L. Elbert | Zendy; Josep Llaveria | Zendy; Penelope E. Streatfeild | Zendy; Edward A. Anderson | Zendy

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

Author(s) -

Felix Urbitsch,

Bryony L. Elbert,

Josep Llaveria,

Penelope E. Streatfeild,

Edward A. Anderson

Publication year - 2020

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c00089

Subject(s) - chemistry , enantioselective synthesis , modular design , natural product , stereochemistry , hybrid , combinatorial chemistry , organic chemistry , catalysis , computer science , biology , botany , operating system

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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