Target-oriented multifunctional organocatalysis for enantioselective synthesis of bicyclo[3.3.1]nona-2,6-dien-9-ones. A formal asymmetric synthesis of huperzine A |
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| Authors: | Xiao-Hua Ding Xiang Li Dan Liu Wei-Chen Cui Xuan Ju Shaozhong Wang Zhu-Jun Yao |
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| Institution: | State Key Laboratory of Coordination Chemistry and Nanjing National Laboratory of Microstructures, School of Chemistry and Chemical Engineering, Nanjing University, 22 Hankou Road, Nanjing, Jiangsu 210093, China |
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| Abstract: | A target-oriented highly enantioselective multifunctional organocatalytic approach has been developed to construct the bicycle-3.3.1]nona-2,6-dien-9-one core of (?)-huperzine A for the first time, with up to 95% ee in the gram-scale procedure. The newly established methodology is also eligible to synthesize a variety of bicyclo3.3.1]nona-2,6-dien-9-ones in high enantiopurities, and thus is useful for the future development of novel huperzine A analogs with medicinal interests. |
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