利用 sp(3) -sp(3) Negishi 交叉偶联反应全合成抗炎和促解决脂质介质 MaR1n-3 DPA。
Total synthesis of the anti-inflammatory and pro-resolving lipid mediator MaR1n-3 DPA utilizing an sp(3) -sp(3) Negishi cross-coupling reaction.
机构信息
School of Pharmacy, Department of Pharmaceutical Chemistry, University of Oslo, PO Box 1068 Blindern, 0316 Oslo (Norway).
出版信息
Chemistry. 2014 Nov 3;20(45):14575-8. doi: 10.1002/chem.201404721. Epub 2014 Sep 15.
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.
摘要
已通过 11 步反应，以 12%的总产率实现了脂质介质 MaR1n-3 DPA（5）的首次全合成。5 的立体选择性制备基于 Pd 催化的 sp(3)-sp(3)Negishi 交叉偶联反应和立体控制的 Evans-Nagao 乙酸酯Aldol 反应。与生物合成的 5 相匹配的 LC-MS/MS 结果。这种新型的脂质介质显示出强大的促解决特性，刺激巨噬细胞吞噬凋亡的中性粒细胞。
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