乙选择性 (+) -阿博里丁的总合成
Zhen Zhang1, Sujun Xie1, Bin Cheng1
1State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering , Lanzhou University , Lanzhou 730000 , China.
Journal of the American Chemical Society
|April 9, 2019
概括
研究人员报告了第一个形化物 (+) - 化的全合成. 这种高效的14步合成利用关键的立体选择反应来构建复杂的双循环核心和四级立体中心.
科学领域:
- 有机化学
- 合成化学
- 自然产品合成
背景情况:
- 形类化合物具有具有重要生物学意义的复杂结构.
- 在有机化学中,像 (+) - 阿博里丁因这样的类化合物的总合成是一个相当大的挑战.
研究的目的:
- 开发天然产品 (+) -阿博里丁的有效和选择性总合成.
- 为复杂的化物结构建立一个可扩展的强大的合成路径.
主要方法:
- 立体选择双曼尼克反应用于构建aza[3.3.1]双循环核.
- 为了设置C10立体中心,
- 形成系统和C3四级中心的分子内 dearomative 化.
- 晚期催化脱碳酸氧化,以安装C11基.
主要成果:
- 实现了14个步骤的 (+) - 阿博里迪宁的不对称总合成.
- 合成迅速构建了aza[3.3.1]双循环核心和两个四元立体中心.
- 关键的转化,包括迈克尔添加和 dearomative 化,成功地被使用.
- 大多数反应都以十度尺度进行,表明可扩展性.
结论:
- 报告的合成提供了一个有效的 (+) - 阿博里丁因的途径.
- 这一策略突显了复杂分子合成中的立体选择反应的力量.
- 合成的可扩展性为进一步研究树脂素及其类似物开辟了道路.
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