Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Chem Asian J. 2011 Feb 1;6(2):534-43. doi: 10.1002/asia.201000494. Epub 2010 Nov 24.
Maresin is a potent anti-inflammatory lipid mediator derived from docosahexaenoic acid (DHA). A highly convergent total synthesis of two proposed structures of C7-epimeric maresins from the four known fragments was achieved in 17 steps. The three key coupling reactions were the BF(3)-mediated alkyne attack on the epoxide, chiral titanium complex-promoted enantioselective alkyne addition to the aldehyde, and a Julia-Kocienski olefination. The two synthesized diastereomers were found to be comparably active in blocking neutrophil infiltration in the acute peritonitis model.
马尿酸是一种源自二十二碳六烯酸（DHA）的强效抗炎脂质介质。通过使用四种已知片段，以 17 步反应实现了具有高度汇聚性的 C7-差向异构马尿酸的两种假设结构的全合成。三个关键的偶联反应是 BF3介导的炔烃对环氧化物的进攻、手性钛络合物促进的对醛的对映选择性炔烃加成反应和 Julia-Kocienski 烯烃化反应。所合成的两种非对映异构体在阻断急性腹膜炎模型中的中性粒细胞浸润方面具有相当的活性。
