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

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.

SUBMITTER: Urbitsch F

PROVIDER: S-EPMC7146891 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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

Urbitsch Felix F Elbert Bryony L BL Llaveria Josep J Streatfeild Penelope E PE Anderson Edward A EA

Organic letters 20200207 4

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 (<i>Z</i>)-alkenes. The modular nature of this approach enables the synthesis of novel resolvin hybrids, opening up opportunities for more-extensive inves ...[more]

PMID: 32031820

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