通过并发宏循环形成的Njaoamine C的总合成
Thomas Varlet1, Sören Portmann1, Alois Fürstner1
1Max-Planck-Institut für Kohlenforschung, 45470 Mülheim/Ruhr, Germany.
Journal of the American Chemical Society
|September 21, 2023
概括
研究人员使用一种新的双环关闭基转基因 (dRCAM) 策略, 首次实现了海洋天然产物Njaoamine C的总合成. 这种创新方法有效地构建复杂的宏循环结构,促进化物合成.
科学领域:
- 有机化学
- 自然产品合成
- 医学化学
背景情况:
- 海洋天然产品如胺C具有复杂的结构和强大的生物活性.
- 现有的曼胺类化合物的合成策略在构建多个宏环时面临挑战.
- 亚胺C的二三环核是一个重要的合成障碍.
研究的目的:
- 实现第一个细胞毒性海洋天然产物胺C的完全合成.
- 开发一种新的合成策略来制造复杂的曼胺类化合物.
- 在复杂分子合成中探索双环关闭基转化 (dRCAM) 的实用性.
主要方法:
- 通过双环关闭基转化 (dRCAM) 同时形成两个宏环.
- 使用具有动态共价化学的基催化剂进行错误校正.
- 采用催化液体化为选择性功能化的.
主要成果:
- 成功的全合成纳胺C.
- 用于同时构建两个宏环的dRCAM的演示.
- 在帕拉催化水分定位中观察到高化学选择性,有利于 (异质) 基.
结论:
- 开发的dRCAM策略提供了一个有效的 njaoamine C 和相关的manzamine 类化合物的途径.
- 动态共价化学和选择性催化是克服复杂化合物合成挑战的关键.
- 这项工作扩大了天然产品合成和药物化学探索的合成工具箱.
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