Scalable Synthesis of Cyclocitrinol,Journal of the American Chemical Society

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Scalable Synthesis of Cyclocitrinol
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2018-07-15 , DOI: 10.1021/jacs.8b06444
Yu Wang ₁ , Wei Ju ₁ , Hailong Tian ₁ , Weisheng Tian ₁ , Jinghan Gui ₁

Affiliation

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.

中文翻译：

环柠檬醇的可扩展合成

报道了从廉价的市售孕烯醇酮合成 C25 类固醇天然产物环柠檬醇的 10 步。该合成采用仿生级联重排，可有效构建具有挑战性的双环[4.4.1] A/B 环系统，仅通过 9 个步骤即可实现双环 [4.4.1] 烯酮中间体 18 的克级合成。这项工作也为环柠檬醇的生物合成来源提供了实验支持。

更新日期：2018-07-15

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