Total Synthesis of (−)-Principinol C

作者：Tianhao Ma, Hao Cheng, Mallesham Pitchakuntla, Weihao Ma, Yanxing Jia · 发表于：Journal of the American Chemical Society · 年份：2022 · DOI：10.1021/jacs.2c08694 · 被引用次数：42 · 研究领域：Bioactive Natural Diterpenoids Research、Marine Sponges and Natural Products、Chemical synthesis and alkaloids

We have achieved the first total synthesis of (-)-principinol C, which possesses an intriguing and complex 5/7/6/5 tetracyclic skeleton with eight contiguous stereocenters. The 5/7/6/5 tetracyclic skeleton of principinol C was assembled using an intramolecular Pauson-Khand reaction as the key step. This synthetic route represents the first application of the intramolecular Pauson-Khand reaction of enyne to construct the 7,5-bicyclic ring system in natural product synthesis.