简短的,对OKARAMINE N的选择性总合成
Phil S Baran1, Carlos A Guerrero, E J Corey
1Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
Journal of the American Chemical Society
|May 8, 2003
概括
研究人员首次实现了对 bis-indole 类化合物 okaramine N 的全合成. 这一突破利用了新的合成策略,包括Pd(II) 介导的循环和光氧化,来构建复杂的分子.
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:
- 双醇类化合物,如甲胺,是具有潜在生物活性的自然产品的一类.
- 奥卡胺的复杂结构对化学合成构成重大挑战.
- 对于获得用于生物评估的纯立体异构体而言,酶选择性合成至关重要.
研究的目的:
- 为了实现第一个enantioselective总合成的okaramine N. N.
- 开发适用于复杂的醇类化合物的新型合成方法.
- 为了提供一个可扩展的路线访问okaramine N及其类型.
主要方法:
- 合N-prenylated三甲衍生物的结合.
- 帕拉 (II) 介导的循环和重新排列.
- 选择性反应,光氧化和热反反应.
主要成果:
- 成功合成了okaramine N (1),从中间产物中获得70%的产量 6.
- 关键的中间体 (2-7) 被合成和表征.
- 开发了一种涉及,光氧化和回反应的新序列.
结论:
- 完成了第一个okaramine N的全合成.
- 开发的合成途径为这种复杂的双醇类化合物提供了有效的访问.
- 该方法可能适用于合成其他相关的自然产品.
相关概念视频
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