基于循环化/碳化/双循环化级联的 (+) - 和 (-) - 巴塞拉丁C 的合成:对绝对配置的修订
Tianci Yue1, Taichi Kusakabe1, Kyoka Someya1
1Faculty of Pharmaceutical Sciences, Toho University, 2-2-1 Miyama, Funabashi, Chiba 274-8510, Japan.
Organic letters
|April 11, 2025
概括
研究人员通过一种新的级联反应合成了瓜尼迪诺化物 (+) - 和 (-) - 巴塞拉丁C. 这种高效的方法构建了复杂的三环瓜尼迪诺核,并修改了天然产品.
科学领域:
- 有机化学 有机化学
- 自然产品的合成自然产品的合成
- 药用化学 医学化学
背景情况:
- 瓜尼迪诺类化合物是一种具有潜在生物活性的海洋天然产品.
- 巴兹拉丁C是一种复杂的瓜尼迪诺化物,从海洋生物中分离出来.
- 有效的合成途径到复杂的类化合物对于进一步的生物研究和潜在的药物开发至关重要.
研究的目的:
- 开发一种新且高效的合成策略,用于对 (+) - 和 (-) - 巴塞拉丁C.的酶选择性合成.
- 以一种立体控制的方式构建巴塞拉丁C的复杂的三环瓜尼迪诺核.
- 根据合成证据,修订天然 (-) - 巴塞拉丁C 的绝对配置.
主要方法:
- 采用了一个关键的循环化/碳化/双循环化级联反应.
- 光学活跃的propargyl guanidine作为起始材料使用.
- 三环瓜尼迪诺核与三个立体中心的立体选择性构造是在单个步骤中实现的.
主要成果:
- 合成成功生成了具有 Ester 功能的三环瓜尼迪诺核.
- 随后的基的转化产生了巴塞拉丁C的两个反体.
- 自然 (-) - 巴塞拉丁C 的绝对配置被重新分配为 (11S,13R,15S).
结论:
- 一种高效的级联反应使得巴塞拉丁C的立体选择性合成成为可能.
- 修订后的绝对配置为自然产品化学领域提供了关键的更新.
- 这种合成方法为访问其他复杂的瓜尼迪诺化物提供了一个有价值的平台.
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