See Yi Yang, Herrmann Aaron T, Aihara Yoshinori, Baran Phil S
Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
J Am Chem Soc. 2015 Nov 4;137(43):13776-9. doi: 10.1021/jacs.5b09463. Epub 2015 Oct 21.
Steroids bearing C12 oxidations are widespread in nature, yet only one preparative chemical method addresses this challenge in a low-yielding and not fully understood fashion: Schönecker's Cu-mediated oxidation. This work shines new light onto this powerful C-H oxidation method through mechanistic investigation, optimization, and wider application. Culminating in a scalable, rapid, high-yielding, and operationally simple protocol, this procedure is applied to the first synthesis of several parent polyoxypregnane natural products, representing a gateway to over 100 family members.
含有C12氧化的甾体类化合物在自然界中广泛存在，但只有一种制备化学方法以低产率且尚未完全理解的方式应对这一挑战：舍内克的铜介导氧化反应。这项工作通过机理研究、优化和更广泛的应用，为这种强大的C-H氧化方法带来了新的启示。最终形成了一种可扩展、快速、高产且操作简单的方案，该方法被应用于几种母体多氧孕甾烷天然产物的首次合成，为100多个家族成员打开了大门。
