总合成 (+/-) - 心理胺
Timothy Newhouse1, Phil S Baran
1Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Journal of the American Chemical Society
|July 29, 2008
概括
一种新型的合成途径通过将阿尼林和胺衍生物结合起来,有效地创建C-3四元化罗英多林结构. 这种方法简化了天然产品psychotrimine的合成,在最小的步骤中实现了高产量.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
- 自然产品的合成自然产品的合成
背景情况:
- 罗林多林结构是各种生物活性化合物的关键结构动图.
- 像psychotrimine这样复杂的天然产品的高效合成仍然是有机化学的一个重大挑战.
研究的目的:
- 开发一种新的,高效的,实用的合成方法来构建C-3四元化罗英林框架.
- 应用这种新的方法来简化复杂的自然产品psychotrimine的合成.
主要方法:
- 确定了三胺衍生物和2- आयो多阿尼林之间的化学选择性合反应.
- 这种反应使用简单的试剂:N-iodosuccinimide (NIS) 和三胺 (TEA).
- 证明了格拉姆尺度合成,突出显示了反应的可扩展性和实用性.
主要成果:
- 成功开发了一种新的工艺,用于将阿尼林与胺衍生物结合起来.
- 这种反应有效地提供了C-3四元化罗英多林结构.
- 复杂的天然产品心理胺从易于获得的托里普坦胺前体中仅用四个步骤合成,获得了41-45%的整体隔离产量.
结论:
- 开发的合成途径为C-3四元化罗英多林合成提供了一种高效和实用的方法.
- 这种方法大大简化了psychotrimine的制备,最大限度地减少了功能组操纵和氧化还原步骤.
- 反应的可扩展性和效率使其对访问复杂的自然产品和相关结构具有价值.
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