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

Yuanyuan Yu, Guang Li, Long Jiang, Liansuo Zu

Angewandte Chemie (International ed. in English) 2015 Oct 19

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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. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Citation

Yuanyuan Yu, Guang Li, Long Jiang, Liansuo Zu. An Indoxyl-Based Strategy for the Synthesis of Indolines and Indolenines. Angewandte Chemie (International ed. in English). 2015 Oct 19;54(43):12627-31