总合成的 (-) - himgaline 的总合成
Unmesh Shah1, Samuel Chackalamannil, Ashit K Ganguly
1Schering-Plough Research Institute, 2015 Galloping Hill Road, Kenilworth, NJ 07033, USA.
Journal of the American Chemical Society
|September 28, 2006
概括
研究人员首次实现了 (-) - himgaline 的总合成和 (-) - GB 13. 的 enantioselective 合成. 这些复杂的分子是使用新型脱碳化阿扎-迈克尔反应和循环化策略合成的.
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:
- (-) - 希姆加林和 (-) - GB 13是复杂的自然产品.
- 这些化合物的高效合成路径对化学研究和潜在应用有价值.
研究的目的:
- 报告第一个 (-) - himgaline 的总合成.
- 开发一种与之相关的化合物 (-) - - GB 13 的高度对抗选择性合成.
主要方法:
- 在酸性条件下利用了对六环乳前体的脱碳化阿扎-迈克尔反应.
- 采用了一个基本的处理方法来合成 (-) -GB 13.
- 进行了酸催化 (-) -GB 13 循环转化为氧林,随后用三氧化进行降解以合成 (-) -林.
主要成果:
- 通过脱碳化阿扎-迈克尔反应,通过80%的产量成功合成了 (-) - - GB 13.
- 通过循环化和立体选择性减少实现了 (-) - himgaline 的独家形成.
结论:
- 建立了第一个 (-) - himgaline 的总合成,证明了一个新的合成途径.
- 开发了一条高度对 (-) - - GB 13 的酶选择性路径,展示了关键反应的实用性.
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