化学
酰胺
烯丙基重排
腈
全合成
烯丙醇
催化作用
立体化学
有机化学
作者
Yan Zhang,Yuye Chen,Manrong Song,Bin Tan,Yujia Jiang,Chongyuan Yan,Yuyang Jiang,Xinyue Hu,Chengqian Zhang,Wenqing Chen,Jing Xu
摘要
Among the famous Daphniphyllum alkaloids family, the calyciphylline A-type subfamily has triggered particular interest from the organic synthesis community in recent years. Here, we report divergent total syntheses of three calyciphylline A-type alkaloids, namely, (−)-10-deoxydaphnipaxianine A, (+)-daphlongamine E, and (+)-calyciphylline R. Our work highlights an efficient, divergent strategy via late-stage divinyl carbinol rearrangements, including an unprecedented oxidative Nazarov electrocyclization using an unfunctionalized tertiary divinyl carbinol and an unusual allylic alcohol rearrangement. A highly efficient "donor–acceptor" platinum catalyst was used for a critical nitrile hydration step. Moreover, the power of selective amide reductions has also been showcased by novel and classic tactics.
科研通智能强力驱动
Strongly Powered by AbleSci AI