An Indoxyl-Based Strategy for the Synthesis of Indolines and Indolenines

Angewandte Chemie
Yuanyuan YuLiansuo Zu

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.

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Citations

Nov 5, 2016·The Journal of Organic Chemistry·Carolyn A LeverettAlbert Padwa
Mar 16, 2017·Organic Letters·Chunyu WangLiansuo Zu
Apr 28, 2017·Journal of the American Chemical Society·Xian-He ZhaoChun-An Fan
May 4, 2017·Angewandte Chemie·Benxiang ZhangChaozhong Li
Jun 14, 2016·Angewandte Chemie·Guang LiLiansuo Zu
Jun 16, 2017·Angewandte Chemie·Yuanyuan YuLiansuo Zu
Mar 29, 2019·The Journal of Organic Chemistry·Valentina PirovanoElisabetta Rossi
Mar 31, 2018·Journal of Natural Products·Chao ZhangXuebin Liao
Jan 30, 2020·Journal of the American Chemical Society·Benxiang ZhangChaozhong Li
Nov 20, 2021·Journal of the American Chemical Society·Wenqiang ZhouMin Zhang

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