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An Indoxyl‐Based Strategy for the Synthesis of Indolines and Indolenines
Author(s) -
Yu Yuanyuan,
Li Guang,
Jiang Long,
Zu Liansuo
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201505173
Subject(s) - indoline , indole test , natural product , combinatorial chemistry , chemistry , reactivity (psychology) , block (permutation group theory) , stereochemistry , mathematics , combinatorics , medicine , alternative medicine , pathology
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.