Abstract
The first total synthesis of the lipid mediator MaR1n-3 DPA(5) has been achieved in 12% overall yield over 11 steps. The stereoselective preparation of 5 was based on a Pd-catalyzed sp3-sp3Negishi cross-coupling reaction and a stereocontrolled Evans-Nagao acetate aldol reaction. LC-MS/MS results with synthetic material matched the biologically produced 5. This novel lipid mediator displayed potent pro-resolving properties stimulating macrophage efferocytosis of apoptotic neutrophils.
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Tungen, J. E., Aursnes, M., Dalli, J., Arnardottir, H., Serhan, C. N., & Hansen, T. V. (2014). Total synthesis of the anti-inflammatory and pro-resolving lipid mediator MaR1n-3 DPAutilizing an sp3-sp3Negishi cross-coupling reaction. Chemistry - A European Journal, 20(45), 14575–14578. https://doi.org/10.1002/chem.201404721
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