Concise Total Synthesis of Salimabromide

作者:Lu, Hai-Hua*; Gan, Kang-Ji; Ni, Fu-Qiang; Zhang, Zhihan; Zhu, Yao
来源:Journal of the American Chemical Society, 2022, 144(41): 18778-18783.
DOI:10.1021/jacs.2c08337

摘要

We achieved a concise total synthesis of salimabromide by using a novel intramolecular radical cyclization to simultaneously construct the unique benzo-fused [4.3.1] carbon skeleton and the vicinal quaternary stereocenters. Other notable transformations include a tandem Michael/Mukaiyama aldol reaction to introduce most of the molecule's structural elements, along with hidden information for late-stage transformations, an intriguing tandem oxidative cyclization of a diene to form the bridged butyrolactone and enone moieties spontaneously, and a highly enantioselective hydrogenation of a cycloheptenone derivative (97% ee) that paved the way for the asymmetric synthesis of salimabromide.