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Biomimetic Synthesis of Oleocanthal, Oleacein, and Their Analogues Starting from Oleuropein, A Major Compound of Olive Leaves.
Journal of Natural Products ( IF 5.1 ) Pub Date : 2020-05-22 , DOI: 10.1021/acs.jnatprod.0c00086
Georgia Sarikaki , Nikoleta Christoforidou , Nicolas Gaboriaud-Kolar , Amos B Smith 1 , Ioannis K Kostakis , Alexios-Leandros Skaltsounis
Affiliation  

Oleocanthal and oleacein are known for a wide range of beneficial activities in human health and the prevention of diseases. The inability to isolate significant and pure amounts of these natural compounds and their demanding synthesis lead to the development of an efficient, five-step, three-pot procedure. The synthesis is performed by a convenient biomimetic approach, starting from oleuropein, an abundant raw material in olive leaves, through the mixed anhydride of oleoside. The method is stereocontrolled and provides an efficient approach to the synthesis of various oleocanthal analogues; thus, a small library of four compounds was prepared with 35–45% overall yield.

中文翻译:

从橄榄叶的主要化合物橄榄苦苷开始仿生合成油橄榄、油橄榄素及其类似物。

Oleocanthal 和 oleacein 以对人类健康和预防疾病的广泛有益活动而闻名。由于无法分离大量纯天然化合物及其合成要求高,因此开发了一种高效的五步三锅法。该合成是通过一种方便的仿生方法进行的,从橄榄叶中丰富的原料橄榄苦苷开始,通过油苷的混合酸酐。该方法是立体控制的,为合成各种油橄榄类似物提供了一种有效的方法;因此,以 35-45% 的总产率制备了一个包含四种化合物的小型文库。
更新日期:2020-06-26
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