环柠檬醇的可扩展合成
Scalable Synthesis of Cyclocitrinol.
作者信息
Wang Yu, Ju Wei, Tian Hailong, Tian Weisheng, Gui Jinghan
机构信息
CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis , Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences , 345 Lingling Road , Shanghai 200032 , China.
出版信息
J Am Chem Soc. 2018 Aug 1;140(30):9413-9416. doi: 10.1021/jacs.8b06444. Epub 2018 Jul 19.
A 10-step synthesis of the C25 steroid natural product cyclocitrinol from inexpensive, commercially available pregnenolone is reported. This synthesis features a biomimetic cascade rearrangement to efficiently construct the challenging bicyclo[4.4.1] A/B ring system, which enabled a gram-scale synthesis of the bicyclo[4.4.1] enone intermediate 18 in only nine steps. This work also provides experimental support for the biosynthetic origin of cyclocitrinol.
报道了一种从廉价的市售孕烯醇酮出发，经10步合成C25甾体天然产物环柠檬醇的方法。该合成方法的特点是通过仿生级联重排高效构建具有挑战性的双环[4.4.1] A/B环系，仅需9步就能实现双环[4.4.1]烯酮中间体18的克级规模合成。这项工作还为环柠檬醇的生物合成起源提供了实验支持。
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