Department of Pharmacology and Toxicology , Michigan State University , East Lansing , Michigan 48824 , United States.
Department of Chemistry , Michigan State University , East Lansing , Michigan 48824 , United States.
J Org Chem. 2019 Dec 6;84(23):15362-15372. doi: 10.1021/acs.joc.9b02378. Epub 2019 Nov 21.
In this study, we report the first asymmetric total synthesis of 19,20-epoxydocosapentaenoic acid (19,20-EDP), a naturally occurring bioactive cytochrome P450 metabolite of docosahexaenoic acid, a major constituent of fish oil. Our strategy involves direct asymmetric epoxidation to produce an enantiopure -epoxyaldehyde that can be appended to the rest of the skipped polyene core by Wittig condensation. Our route is step-economical and late divergent and could be an appealing method by which to synthesize EDP analogues for biological studies.
在这项研究中，我们报告了 19,20-环氧二十二碳五烯酸（19,20-EDP）的首次不对称全合成，19,20-EDP 是二十二碳六烯酸（一种主要存在于鱼油中的物质）的一种生物活性细胞色素 P450 代谢产物。我们的策略涉及直接不对称环氧化，以产生对映体纯的 -环氧化醛，该醛可以通过Wittig 缩合连接到其余的 skipped 多烯核心上。我们的路线具有经济性和后期发散性，可以作为合成 EDP 类似物进行生物学研究的一种有吸引力的方法。
