Key Laboratory of Bioorganic Chemistry and Molecular Engineering, Ministry of Education and Beijing National Laboratory for Molecular Science, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China.
Peking-Tsinghua Center for Life Sciences, Academy for Advanced Interdisciplinary Studies, Peking University, Beijing 100871, China.
J Am Chem Soc. 2022 Aug 31;144(34):15462-15467. doi: 10.1021/jacs.2c06934. Epub 2022 Aug 22.
A new and enantioselective total synthesis of the diterpenoid (+)-mutilin is described. Following a Claisen rearrangement approach to construct the 6,9-bicycle, a transannular [2+2] photocycloaddition and the ensuing ring-opening reaction were implemented to forge the characteristic 5-6-8 propellane-like skeleton. Subsequent late-stage alkylations and reduction completed the synthesis.
描述了一种新型的、对映选择性的二萜（+）-mutilin 全合成方法。在采用 Claisen 重排方法构建 6,9-双环之后，进行了反式环加成和随后的开环反应，形成了特征性的 5-6-8 类轮烷骨架。随后的晚期烷基化和还原完成了合成。
