通过电化学循环的Dragocins A-C的总合成
Brendyn P Smith1, Nathanyal J Truax1, Alexandros S Pollatos1
1Department of Chemistry, Scripps Research, 10550 N. Torrey Pines Road, La Jolla, California 92037, United States.
Angewandte Chemie (International ed. in English)
|February 15, 2024
概括
研究人员首次实现了A-C龙的总合成,这些复杂的天然产品具有独特的氧化核糖和pyrrolidine环. 这项工作展示了新的合成策略,包括用于构建核心结构的电化学方法.
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:
- 德拉古辛A-C是复杂的天然产品,具有独特的C4'氧化核糖和多氧化罗利丁环.
- 德拉古辛的复杂结构对总合成提出了重大挑战.
研究的目的:
- 为了实现第一个完全合成的龙A-C.
- 开发新的合成方法来构建复杂的自然产品.
- 探索电化学氧化在天然产品合成中的实用性.
主要方法:
- 多步骤的总合成涉及立体控制的罗利丁结构.
- 对于9个成员的环形形成而进行的灾难选择性氧化电化学循环.
- 探索合成路径的生成,包括诸如C-H氧化等失败的尝试.
主要成果:
- 成功地完成了甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基甲基
- 开发一个快速的,立体控制的路径到一个功能化的pyrrolidine.
- 采用了前所未有的二聚体选择性氧化电化学循环,形成了9个环.
- 演示开发的电化学氧化协议的一般实用性.
结论:
- 完成了第一个甲-C 龙素的全合成.
- 新的合成策略,包括一个关键的电化学循环,已成功实施.
- 开发的电化学氧化协议显示了在有机合成中更广泛的应用的前景.
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
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