混合尼菲林B的总合成
Wenhao Zhang1, Ming Ding1, Jian Li1
1State Key Laboratory of Bioorganic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis , Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , China.
Journal of the American Chemical Society
|March 2, 2018
概括
研究人员首次完全合成了复杂的多夫尼类化物Hybridaphniphylline B. 这一突破利用了后期的分子间迪尔斯-阿尔德反应,推进了合成有机化学.
科学领域:
- 有机化学
- 自然产品合成
- 医学化学
背景情况:
- 混合尼菲林B是一种复杂的Daphniphyllum化物,具有11个环和19个立体中心.
- 混合尼菲林B的复杂结构为总合成带来了重大挑战.
研究的目的:
- 报告第一个混合尼菲林B的全合成.
- 开发一个可扩展的关键中间体路径,包括达芬龙B.
- 探索新的合成策略,如晚期的分子间迪尔斯-阿尔德反应.
主要方法:
- 建立了一个可扩展的达芬隆格兰B路径.
- 一个关键的克莱森重组被优化,以抑制不必要的科普重组.
- 这种合成涉及循环二烯和阿斯普鲁酸衍生物之间的后期分子间迪尔斯-阿尔德反应.
- 开发了一种用于二烯形成和迪尔斯-阿尔德反应的单方案.
主要成果:
- 首次成功完成基尼菲林B的全合成.
- 还合成了达氨酸E和脱水达氨酸B.
- 合成证明了晚期分子间迪尔斯-阿尔德反应在构建复杂的化物框架中的实用性.
- 一个新的单协议简化了二烯形成和循环添加过程.
结论:
- 混合尼菲林B的总合成为天然产品合成领域提供了宝贵的贡献.
- 开发的合成策略为获得其他复杂的Daphniphyllum化物提供了潜力.
- 这项研究突显了迪尔斯-阿尔德反应在组装复杂分子结构方面的力量.
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