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Highly Enantioselective Semisynthesis of (+)/(-)-Gossypol Schiff Base Derivatives from Ground Plant Material.
Journal of Natural Products ( IF 5.1 ) Pub Date : 2019-07-11 , DOI: 10.1021/acs.jnatprod.8b01045
Mohamed V Sidi Boune 1, 2 , Brahim Elemine 2 , Ahmed Aliyenne 1, 3 , Abderrahmane Hadou 2 , Adam Daïch 1 , Mohamed Othman 1 , Ata M Lawson 1
Affiliation  

We have recently developed a one-pot process for simultaneous extraction and chemical modification (SECheM) on Cienfuegosia digitata, a Mauritanian Malvaceae called locally "Izide". On the basis of this innovative methodology that consisted of using ground plant roots as starting material in gossypol Schiff base semisynthesis, we now report how this concept can be used to access enantiomerically pure Schiff base atropisomer derivatives of gossypol in only two steps. This study has been envisioned since enantiomerically pure Schiff base atropisomer derivatives of gossypol are generally more potent biologically when compared to racemic gossypol Schiff bases.

中文翻译:

地面植物材料的(+)/(-)-棉酚席夫碱衍生物的高度对映选择性半合成。

我们最近开发了一种一锅法,用于在指称木瓜(Curifuegosia digitata)上同时进行提取和化学修饰(SECheM),毛里塔尼亚的锦葵科在当地被称为“伊齐德”。基于这种创新的方法,该方法包括在棉酚Schiff碱半合成中使用地面植物的根部作为起始原料,我们现在报告该概念如何仅用两步即可用于获得对映体纯的棉酚的Schiff碱阻转异构体衍生物。由于棉酚的对映体纯席夫碱阻转异构体衍生物与消旋棉酚席夫碱相比在生物学上通常更有效,因此可以预见该研究。
更新日期:2019-07-11
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