Organocatalytic Asymmetric One‐Step Desymmetrizing Dearomatization Reaction of Indoles: Development and Bioactivity Evaluation. Issue 1 (4th December 2018)

• Record Type: Journal Article
• Authors: Peng, Lei; Xu, Da; Yang, Xiaohong; Tang, Jiakun; Feng, Xuli; Zhang, Shao‐Lin; Yan, Hailong
• Is Part Of: Angewandte Chemie international edition. Volume 58:Issue 1(2018)
• Page Start: 216
• Page End: 220
• Publication Date: 2018-12-04
• Subjects: anticancer -- cycloaddition -- dearomatization -- heterocycles -- organocatalysis; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201811437
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: 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. Abstract : All set : 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 high yields with excellent diastereo‐ and enantioselectivities. Moreover, product1 inhibited the proliferation of all tested cancer cells, but showed marginal effects against non‐cancerous cells.