Stereocontrolled total synthesis of neuroprotectin D1 / protectin D1 and its aspirin-triggered stereoisomer.
Stereocontrolled total synthesis of neuroprotectin D1 / protectin D1 and its aspirin-triggered stereoisomer.
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DOI：
10.1016/j.tetlet.2012.01.032
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发表时间：
2012-04-04
影响因子：
1.8
通讯作者：
Serhan, Charles N.
中科院分区：
文献类型：
--
作者：
Petasis, Nicos A.;Yang, Rong;Winkler, Jeremy W.;Zhu, Min;Uddin, Jasim;Bazan, Nicolas G.;Serhan, Charles N.
Neuroprotectin D1/protectin D1 是一种有效的抗炎、促消退和神经保护脂质介质，由二十二碳六烯酸生物合成，通过全有机合成制备对映体纯形式。该合成策略是高度立体控制和收敛的，其特征是缩水甘油起始材料的环氧化物开环以引入10(R)和17(S)羟基。通过炔前体的顺式还原来确保所需的烯烃 Z 几何结构，同时在末端引入共轭 E,E,Z 三烯，以最大限度地减少 Z/E 异构化。相同的策略也用于具有17(R)-立体化学的阿司匹林触发的神经保护素D1/保护素D1的全合成。用所报道的方法获得的合成化合物与内源性衍生材料相匹配，并有助于建立其完整的立体化学。
Neuroprotectin D1 / protectin D1, a potent anti-inflammatory, proresolving, and neuroprotective lipid mediator derived biosynthetically from docosahexaenoic acid, was prepared in enantiomerically pure form via total organic synthesis. The synthetic strategy is highly stereocontrolled and convergent, featuring epoxide opening of glycidol starting materials for the introduction of the 10(R) and 17(S) hydroxyl groups. The desired alkene Z geometry was secured via the cis-reduction of alkyne precursors, while the conjugated E,E,Z triene was introduced at the end, in order to minimize Z/E isomerization. The same strategy, was also employed for the total synthesis of aspirin-triggered neuroprotectin D1 / protectin D1 having the 17(R)-stereochemistry. Synthetic compounds obtained with the reported method were matched with endogenously derived materials, and helped establish their complete stereochemistry.
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营养中的Docosahexaenoic酸信号脂肪组学：衰老，神经炎症，黄斑变性，阿尔茨海默氏症和其他神经退行性疾病的重要性。
影响因子：
8.9
作者：
Bazan NG;Molina MF;Gordon WC
通讯作者：
Gordon WC
影响因子：
62.1
作者：
Serhan, Charles N.;Petasis, Nicos A.
通讯作者：
Petasis, Nicos A.
影响因子：
4.4
作者：
Serhan, CN;Gotlinger, K;Petasis, NA
通讯作者：
Petasis, NA
DOI：
10.1016/j.jasms.2006.09.002
发表时间：
2007-01-01
影响因子：
3.2
作者：
Hong, Song;Lu, Yan;Serhan, Charles N.
通讯作者：
Serhan, Charles N.
影响因子：
3.7
作者：
Zhao Y;Calon F;Julien C;Winkler JW;Petasis NA;Lukiw WJ;Bazan NG
通讯作者：
Bazan NG