Key Laboratory of Applied Surface and Colloid Chemistry & School of Chemistry and Chemical Engineering, Shaanxi Normal University, 620 West Chang'an Ave, Xi'an, 710119, China.
CAS Key Lab of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Ling Ling Road, Shanghai 200032, China.
Org Lett. 2021 Dec 17;23(24):9659-9663. doi: 10.1021/acs.orglett.1c03943. Epub 2021 Dec 7.
Herein, we report the highly efficient total syntheses of galanthamine and lycoramine from a common tetracyclic intermediate. This concise synthetic route features a two-phase strategy, which includes the early-stage rapid construction of a tetracyclic skeleton followed by the late-stage selective reorganization of the tetracyclic skeleton. Key to the success of this strategy are a palladium-catalyzed carbonylative cascade annulation, a DDQ-mediated intramolecular regioselective oxidative lactamization, as well as a BF·EtO-promoted reorganization of the bridged tetracyclic skeleton.
在此，我们报告了从一个共同的四环中间体高效全合成石蒜碱和加兰他敏。这条简洁的合成路线采用两相策略，包括早期快速构建四环骨架，然后晚期选择性重排四环骨架。该策略成功的关键在于钯催化的羰基化串联环化反应、DDQ 介导的分子内区域选择性氧化内酰胺化反应，以及 BF·EtO 促进桥环四环骨架的重排。
