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.
Highlights
Resolvins D3 and E1 are important signaling molecules in the resolution of inflammation
Since numerous diseases are associated with chronic or excessive inflammation,[2] there is great interest in the synthesis of these natural products in order to develop a deeper understanding of their individual roles.,1b3 Resolvins D3 (RvD3, 1) and E1 (RvE1, 2) are typical examples of these polyhydroxylated lipid mediators, with the former being the most potent member of the family.[4]
Subsequent to their initial discovery and isolation by Serhan et al.,[5] the structures and stereochemistry of RvD3 and RvE1 were confirmed by Petasis and Serhan via total synthesis.[6]
Summary
Elbert − Chemistry Research Laboratory, Oxford OX1 3TA, United Kingdom. Josep Llaveria − UCB Pharma, Ltd., Slough SL1 3WE, United Kingdom; orcid.org/0000-0003-2260-3657. Streatfeild − Chemistry Research Laboratory, Oxford OX1 3TA, United Kingdom.
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