Total Synthesis and Bioactivities of Two Proposed Structures of Maresin
Total Synthesis and Bioactivities of Two Proposed Structures of Maresin
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DOI：
10.1002/asia.201000494
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发表时间：
2011-02-01
影响因子：
4.1
通讯作者：
Inoue, Masayuki
中科院分区：
文献类型：
--
作者：
Sasaki, Kenji;Urabe, Daisuke;Inoue, Masayuki
Maresin是一种有效的抗炎脂质介质，来源于二十二碳六烯酸（DHA）。一个高度收敛的全合成两个建议的结构的C7-差向异构maresins从四个已知的片段，在17个步骤中实现。三个关键的偶联反应是BF 3介导的炔攻击的环氧化物，手性钛络合物促进的对映选择性炔加成的醛，和Julia-Kocienski烯烃化。在急性腹膜炎模型中，发现两种合成的非对映异构体在阻断中性粒细胞浸润方面具有抑制活性。
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 BF3-mediated alkyne attack on the epoxide, chiral titanium complex-promoted enantioselective alkyne addition to the aldehyde, and a Julia-Kocienski olefination. The two synthesized dia-stereomers were found to be comparably active in blocking neutrophil infiltration in the acute peritonitis model.