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欧尼明和欧尼米诺八酸盐的总合成

Yinghua Wang¹, Toshiya Nagai¹, Itsuki Watanabe¹

¹Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo, 113-0033, Japan.

Journal of the American Chemical Society

|December 6, 2021

概括

研究人员首次完全合成了具有潜在抗HIV和P-糖蛋白抑制作用的复杂天然产物euonymine (1) 和euonyminol octaacetate (2). 这一突破为进一步的生物研究提供了这些具有挑战性的分子.

科学领域:

有机化学
自然产品合成
医学化学

背景情况:

欧胺 (1) 和欧胺醇乙酸 (2) 是由欧胺醇 (3) 衍生而来的复杂天然产品.
这些化合物具有显著的生物活性,包括抗HIV和P- 糖蛋白抑制.
(1) 和 (2) 的复杂结构,具有多个立体中心和氧功能,构成了相当大的合成挑战.

研究的目的:

开发一种有效的,对欧胺 (1) 和欧胺醇乙酸 (2) 的总合成策略.
为两种化合物的合成建立一个共同的中间体.
为了进一步对这些天然产品进行生物评估.

主要方法:

从 (R) - 甘油乙化物开始的酶选择性总合成.
使用迪尔斯-阿尔德反应,分子内化和环闭基转化构建ABC环系统.
通过基板控制的C-C和C-O键形成,对10个立体中心进行立体选择性安装.
晚期功能化包括全球去除保护,乙化,选择性双化, [3+2] 循环添加和还原性脱硫.

主要成果:

欧胺 (1) 和欧胺醇八酸的成功合成.
开发一种共同的中介物,即受保护的euonyminol (5),以促进两种目标的合成.
展示用于构建复杂的多环和宏环结构的新反应序列.

结论:

开发的合成策略提供了有效的euonymine (1) 和euonyminol八酸盐 (2).
这项工作克服了重要的合成挑战,包括安装众多立体中心和宏观循环形成.
合成的化合物现在可用于全面的生物研究, 以探索它们的治疗潜力.

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