D3-trishomocubanetrione synthesis and optical resolution |
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| Affiliation: | 1. Institute of Functional Nano & Soft Materials (FUNSOM), Jiangsu Key Laboratory for Carbon-Based Functional Materials & Devices, Soochow University, Suzhou, Jiangsu 215123, China;2. Shandong Province Key Laboratory of Medical Physics and Image Processing Technology, School of Physics and Electronics, Shandong Normal University, 250014 Jinan, China;3. Coordination Chemistry Institute, State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing National Laboratory of Microstructures, Nanjing University, Nanjing 210023, China;4. College of Electrical and Information Engineering, Shaanxi University of Science and Technology, Xi''an, Shaanxi 710021, China;5. State Key Laboratory of Structural Chemistry, Fujian Institute of Research on Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 35002, China;1. Ningbo Institute of Materials Technology and Engineering, Chinese Academy of Sciences, Ningbo 315201, China;2. Center of Materials Science and Optoelectronics Engineering, University of Chinese Academy of Sciences, Beijing 100049, China;3. Department of Chemical and Environmental Engineering, Faculty of Science and Engineering, University of Nottingham Ningbo China, Ningbo 315100, China;4. CAS Key Laboratory of Nanosystem and Hierarchical Fabrication, CAS Center for Excellence in Nanoscience, National Center for Nanoscience and Technology, Beijing 100190, China;5. School of Materials Science and Engineering, Zhengzhou University, Zhengzhou 450001, China;6. Nottingham Ningbo China Beacons of Excellence Research and Innovation Institute, No. 211 Xingguang Road, Ningbo 315100, China;7. Key Laboratory for Carbonaceous Wastes Processing and Process Intensification Research of Zhejiang Province, Department of Chemical and Environmental Engineering, The University of Nottingham Ningbo China, 199 Taikang East Road, Ningbo 315100, China;1. Key Laboratory of Agro-food Safety and Quality of Ministry of Agriculture and Rural Affairs, Institute of Quality Standard and Testing Technology for Agro-Products, Chinese Academy of Agricultural Sciences, Beijing 100081, China;2. College of Life Science and Technology, Beijing University of Chemical Technology, Beijing 100029, China;3. Beijing National Laboratory for Molecular Sciences, State Key Laboratory of Polymer Physics and Chemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China;4. University of Chinese Academy of Sciences, Beijing 100049, China;1. Key Laboratory of Advanced Civil Engineering Materials, School of Materials Science & Engineering, Tongji University, Shanghai, 201804, China;2. Department of Polymer Materials, School of Materials Science & Engineering, Tongji University, Shanghai, 201804, China;3. School of Automotive Studies, Tongji University, Shanghai, 201804, China |
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| Abstract: | ![]()
A large-scale synthesis for the title compound rac-1 based on 11-oxahexacyclo-[5.4.1.02,6.03,10.04,8.09,12] dodecan-5-one (12) as the key intermediate and an efficient procedure for the optical resolution of rac-1 via the diastereomeric ketals with (R,R)-2,3-butandiol are reported. The absolute configuration is established by correlating the optically pure (+)-trione ([α]D +949°) with (-)-trishomocubane. |
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