乙选择性 (-) - 阿库丁因总合成
Wei Nie1, Jing Gong1, Zhihao Chen1
1Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy , Sichuan University , Chengdu 610041 , P.R. China.
Journal of the American Chemical Society
|May 29, 2019
概括
研究人员首次完成了复杂的类素阿库丁宁的全合成. 这一突破涉及到构建关键结构特征的新策略.
科学领域:
- 有机化学
- 自然产品合成
- 医学化学
背景情况:
- 迪特类类化合物,如阿库丁因,是具有潜在生物活性的复杂自然产品.
- 这些化合物的复杂结构对总合成构成重大挑战.
- 之前的合成努力还没有实现氨酸的完全合成.
研究的目的:
- 为了实现第一个C20-diterpenoid类化合物arcutinine的完全合成.
- 开发新的合成策略来构建复杂的化物框架.
- 用于制备白素的纯白素和纯白素.
主要方法:
- C4四元中心和pyrrolidine E环的早期构造.
- 不对称的结合加法/阿尔多尔级联,用于建立周边四元立体中心 (C4和C5).
- 脱碳聚合,分子内阿扎-瓦克尔循环,氧化脱氧化/分子内迪尔斯-阿尔德级联,-烯酸循环.
主要成果:
- 在racemic和不对称的形式中成功合成了arcutinine.
- 有效地构建了C4四元中心和pyrrolidine E环.
- 在C4和C5形成邻近的全碳四元立体中心.
结论:
- 开发的合成途径为获得阿库丁宁和相关的二类化物提供了一个强大的平台.
- 证实了关键结构动机的早期建设的战略重要性.
- 这项工作扩大了复杂天然产品合成的工具箱.
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