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.
J Am Chem Soc. 2020 Mar 18;142(11):5007-5012. doi: 10.1021/jacs.0c00363. Epub 2020 Mar 6.
A concise bioinspired synthesis of nortriterpenoid propindilactone G has been accomplished from a readily accessible steroidal lactone. Key transformations include a Breslow remote functionalization, a Suárez remote radical functionalization, a ring expansion enabled by a Wagner-Meerwein rearrangement, a stereoinversion of a tertiary alcohol, and a biomimetic transesterification/oxa-Michael addition cascade. This work also provides experimental evidence of the putative propindilactone G biosynthesis pathway.
已从易得的甾体内酯简洁仿生合成得到了新三萜 propindilactone G。关键转化包括 Breslow 远程官能化、Suárez 远程自由基官能化、Wagner-Meerwein 重排实现的环扩张、叔醇的立体反转，以及仿生酯交换/氧杂-Michael 加成级联。这项工作还提供了推测的 propindilactone G 生物合成途径的实验证据。
