期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 54, 期 43, 页码 12627-12631出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201505173
关键词
aza-pinacol rearrangement; indolenines; indolines; indoxyl; synthetic methods
资金
- Tsinghua University
- 1000 Talents Recruitment Program
- Collaborative Innovation Center for Biotherapy (Tsinghua University)
- Collaborative Innovation Center for Biotherapy (Sichuan University)
- National Natural Science Foudation of China [21302107]
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.
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