Total Synthesis of the Indole Alkaloid (±)- and (+)-Methyl N-Decarbomethoxychanofruticosinate†
Yi Wei
State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 (China)
Search for more papers by this authorDuo Zhao
State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 (China)
Search for more papers by this authorCorresponding Author
Prof. Dr. Dawei Ma
State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 (China)
State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 (China)===Search for more papers by this authorYi Wei
State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 (China)
Search for more papers by this authorDuo Zhao
State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 (China)
Search for more papers by this authorCorresponding Author
Prof. Dr. Dawei Ma
State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 (China)
State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 (China)===Search for more papers by this authorThe authors are grateful to National Basic Research Program of China (973 Program, grant 2010CB833200), Chinese Academy of Sciences, and the National Natural Science Foundation of China (grant 21132008 & 20921091) for their financial support.
Graphical Abstract
All caged up: The first total synthesis of N-decarbomethoxychanofruticosinate (see figure) is achieved by using a SmI2-mediated intramolecular Reformatsky-like reaction to create the seven-membered ring, and an intramolecular oxidative coupling to install the caged and strained ring system.
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