A transition metal-free approach to a regioselective total synthesis of the natural product derivative 6-methylellipticine,a potent anticancer agent |
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| Institution: | 1. Tea Research Institute, Chinese Academy of Agricultural Sciences, Hangzhou 310008, China;2. Key Laboratory of Tea Biology and Resources Utilization, Ministry of Agriculture, Hangzhou 310008, China;3. Department of Chemistry, Zhejiang University, Hangzhou 310027, China;1. Department of Chemistry, Kyonggi University, 154-42 Gwanggyosan-ro, Yeongtong-gu, Suwon 16227, Republic of Korea;2. Department of Anatomy and Neurobiology, College of Medicine, Kyung Hee University 26, Kyungheedae-ro, Dongdaemun-gu, Seoul 02447, Republic of Korea;1. College of Resource and Environment, Henan Agricultural University, Zhengzhou 450002, PR China;2. School of Science, Henan Agricultural University, Zhengzhou 450002, PR China;1. School of Pharmaceutical Sciences, Jinzhou Medical University, Jinzhou 121001, China;2. The First Affiliated Hospital of Jinzhou Medical University, Jinzhou 121001, China;3. State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, China;1. Department of Chemistry, Bharathiar University, Coimbatore 641046, India;2. Department of Chemistry, Youngstown State University, 1 University Plaza, Youngstown, OH 44555, USA |
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| Abstract: | A transition metal-free and regioselective total synthesis of 6-methylellipticine, a potent anticancer agent, was developed. This synthetic approach mainly involved two key reactions: a direct amination of multi-functional phenol via an alkylation-Smiles rearrangement protocol, and an intramolecular C–H bond arylation reaction promoted by potassium tert-butoxide. These reactions resulted in the formation of two key intermediates, diarylamine and carbazole derivative, under transition metal-free conditions. The last cyclization afforded the target product 6-methylellipticine. |
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| Keywords: | Transition metal-free Total synthesis 6-Methylellipticine |
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