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Chemistry. 2014 Nov 3;20(45):14575-8. doi: 10.1002/chem.201404721. Epub 2014 Sep 15.

Total synthesis of the anti-inflammatory and pro-resolving lipid mediator MaR1n-3 DPA utilizing an sp(3) -sp(3) Negishi cross-coupling reaction.

Author information

1
School of Pharmacy, Department of Pharmaceutical Chemistry, University of Oslo, PO Box 1068 Blindern, 0316 Oslo (Norway).

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 sp(3) -sp(3) Negishi 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.

KEYWORDS:

cross-coupling; inflammation; natural products; palladium; total synthesis

PMID:
25225129
PMCID:
PMC4232850
DOI:
10.1002/chem.201404721
[Indexed for MEDLINE]
Free PMC Article

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