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Organocatalytic Asymmetric One‐Step Desymmetrizing Dearomatization Reaction of Indoles: Development and Bioactivity Evaluation
Author(s) -
Peng Lei,
Xu Da,
Yang Xiaohong,
Tang Jiakun,
Feng Xuli,
Zhang ShaoLin,
Yan Hailong
Publication year - 2019
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.201811437
Subject(s) - chemistry , indoline , combinatorial chemistry , cancer cell lines , quinone , enantioselective synthesis , organocatalysis , cancer cell , stereochemistry , organic chemistry , catalysis , cancer , biology , genetics
An organocatalytic one‐step desymmetrizing dearomatization reaction of indoles with in situ formed vinylidene ortho ‐quinone methides is reported. A set of [6‐6‐5] and/or [5‐6‐5] fused indoline heterocycles were obtained in excellent yields with excellent diastereoselectivities (>20:1 d.r.) and enantioselectivities (up to 99 % ee ). Moreover, some of the obtained products were screened against a panel of cancer cell lines, and one was identified to inhibit the proliferation of all the tested cancer cells, but showed marginal effects against non‐cancerous cells. The methodology provides a platform for the synthesis of new leading compounds with antitumor activity.