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Organocatalytic Asymmetric One-Step Desymmetrizing Dearomatization Reaction of Indoles: Development and Bioactivity
Lei Peng1, Da Xu1, Xiaohong Yang1
1Chongqing Key Laboratory of Natural Product Synthesis, and Drug Research, School of Pharmaceutical Sciences, Chongqing University, Chongqing, 401331, P. R. China.
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.
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