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An Indoxyl‐Based Strategy for the Synthesis of Indolines and Indolenines |
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| Authors: | Yuanyuan Yu Dr Guang Li Long Jiang Prof?Dr Liansuo Zu |
| Affiliation: | 1. Department of Pharmacology and Pharmaceutical Sciences, School of Medicine, Tsinghua University, Beijing, 100084 (China);2. Collaborative Innovation Center for Biotherapy, State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, West China Medical School, Sichuan University, Chengdu (China) |
| Abstract: | An indoxyl‐based strategy for the synthesis of indolines and indolenines via unprecedented aza‐pinacol and aza‐semipinacol rearrangements was developed. This method provides direct access to the core structures of several classes of indole alkaloids. The synthetic utility was demonstrated by the divergent synthesis of an array of functionalized polycyclic structures from a common intermediate and the formal total synthesis of the indoline natural product minfiensine. The reversed reactivity of indoxyl as a building block compared to that of indole offers a conceptually distinct disconnection strategy for indoline‐ and indolenine‐containing heterocycles and natural products. |
| Keywords: | aza‐pinacol rearrangement indolenines indolines indoxyl synthetic methods |
