Bioinspired Stereoselective Total Synthesis of the Caged Sesquiterpenoid Daphnepapytone A

作者：ZhongXiang Zhang, Pengfei Yu, Wei Chen, Jia Li, Kai Liu, Xingang Xie, Huilin Li, Xuegong She · 发表于：Organic Letters · 年份：2025 · DOI：10.1021/acs.orglett.5c01509 · 被引用次数：8 · 研究领域：Chemical synthesis and alkaloids、Alkaloids: synthesis and pharmacology、Oxidative Organic Chemistry Reactions

The first total synthesis of the novel caged sesquiterpenoid daphnepapytone A is disclosed. Key reactions include a Pauson-Khand cycloaddition to provide oleodaphone, a bioinspired photoinduced [2 + 2] cycloaddition to forge the cyclobutane-containing caged skeleton, and a C-H oxidation and reduction protocol to generate daphnepapytone A. Finally, the 17-step synthetic sequence is shortened to 4 steps in protecting group-free and exclusively stereoselective fashion.