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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• 作者：Xiao-Hua Ding ; Xiang Li ; Dan Liu ; Wei-Chen Cui ; Xuan Ju ; Shaozhong Wang ; Zhu-Jun Yao ; ^{yaoz@nju.edu.cn}
• 关键词：(&minus ; )-Huperzine A ; Multifunctional organocatalysis ; Michael addition ; Enantioselectivity ; Target-oriented methodology
• 刊名：Tetrahedron
• 出版年：2012
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：5 August, 2012
• 卷：68
• 期：31
• 页码：6240-6248
• 文件大小：664 K

摘要

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 (鈭?-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 bicyclo[3.3.1]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.