Construction of the A/B/C core of mexicanolides via a tandem double-aldol reaction |
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| Institution: | 1. Université de Toulouse, UPS, LHFA, CNRS UMR 5069, 118 Route de Narbonne, F-31062 Toulouse, France;2. Institutul de Chimie, Raluca Ripan, Universitatea Babeş-Bolyai, Str. M. Kogălniceanu, Nr: 1, RO-400084 Cluj-Napoca, Romania;3. Université de Toulouse, UPS, Institut de Chimie de Toulouse, ICT-FR2599, 118 Route de Narbonne, F-31062 Toulouse, France;4. LISBP/INSAT, UMR5504, UMR792, CNRS, INRA, INSA, 135 Avenue de Rangueil, 31077 Toulouse Cedex 04, France;5. Facultatea de Chimie şi Inginerie Chimică, Universitatea Babeş-Bolyai, Str. M. Kogălniceanu, Nr: 1, RO-400084 Cluj-Napoca, Romania;1. The Key Laboratory of Optoelectronic Technology & System, Education Ministry of China, Chongqing University, 400044, China;2. College of Opto-electronic Engineering, Chongqing University, 400044, China;3. Chongqing Engineering Research Center of Graphene Film Manufacturing, Chongqing, 401329, China;1. School of Artificial Intelligence, Chongqing Technology and Business University, Chongqing 400067, China;2. College of Optoelectronic Engineering, Key Laboratory of Optoelectronic Technology and Systems, Ministry of Education, Key Disciplines Lab of Novel Micro-Nano Devices and System Technology, Chongqing University, Chongqing 400044, China;3. School of Intelligent Manufacturing, Sichuan University of Arts and Science, Dazhou 635000, China;1. School of Chemistry and Chemical Engineering, Chongqing University, Chongqing 401331, China;2. Analytical and Testing Center, Chongqing University, Chongqing 400044, China;3. Guizhou Provincial Key Laboratory of Computational Nano-Material Science, Guizhou Education University, Guiyang 550018, China;4. National-municipal Joint Engineering Laboratory for Chemical Process Intensification and Reaction, Chongqing 400044, China;1. College of Environment and Ecology, Chongqing University, Chongqing, 400045, China;2. National Base of International Science and Technology Cooperation for Intelligent Manufacturing Service, Chongqing Key Laboratory of Catalysis & New Environmental Materials, Chongqing Technology and Business University, Chongqing, 400067, China;3. Chongqing South-to-Thais Environmental Protection Technology Research Institute Co., Ltd., Chongqing, 400060, China |
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| Abstract: | An efficient and concise approach for rapid assembly of the ABC tricyclic carbon skeleton of mexicanolide-type limonoids is described. The acetal/ketal diketoester precursors were prepared from simple starting materials by LiOH-mediated Michael reactions. The ABC tricyclic skeleton bearing multiple stereogenic centers was efficiently constructed by a powerful one-pot cascade reaction, which includes acetal/ketal hydrolysis, double intramolecular aldol condensation, and alkene migration. |
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| Keywords: | Limonoid Mexicanolide Cascade reaction Aldol reaction |
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