Department of Chemistry, Michigan State University, E. Lansing, MI, 48824, USA.
Angew Chem Int Ed Engl. 2019 Jul 22;58(30):10110-10113. doi: 10.1002/anie.201900340. Epub 2019 Apr 10.
The synthesis of (-)-salinosporamide A, a proteasome inhibitor, is described. The synthesis highlights the assembly of a densely decorated pyrrolidinone core via an aza-Payne/hydroamination sequence. Central to the success of the synthesis is a late-stage C-H insertion reaction to functionalize a sterically encumbered secondary carbon. The latter functionalization leads to an enabling transformation where most of the prototypical strategies failed.
（-）-salinosporamide A 的全合成，一种蛋白酶体抑制剂，被描述。该合成的重点是通过氮杂-Payne/氢胺化序列来组装一个密集装饰的吡咯烷酮核心。该合成的关键是在晚期的 C-H 插入反应中，对一个空间位阻较大的二级碳进行功能化。后者的功能化导致了一种有效的转化，而大多数典型的策略都失败了。
