Total Syntheses of Daphenylline,Daphnipaxianine A,and Himalenine D |
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| Authors: | Lu Ren Dr Jian Li Prof?Dr Ang Li |
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| Institution: | State Key Laboratory of Bioorganic and Natural Products Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, China |
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| Abstract: | We report the total syntheses of daphenylline ( 1 ), daphnipaxianine A ( 5 ), and himalenine D ( 6 ), three Daphniphyllum alkaloids from the calyciphylline A subfamily. A pentacyclic triketone was prepared by using atom‐transfer radical cyclization and the Lu 3+2] cycloaddition as key steps. Inspired by the proposed biosynthetic relationship between 1 and another calyciphylline A type alkaloid, we developed a ring‐expansion/aromatization/aldol cascade to construct the tetrasubstituted benzene moiety of 1 . The versatile triketone intermediate was also elaborated into 5 and 6 through a C=C bond migration/aldol cyclization approach. |
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| Keywords: | alkaloids arene synthesis bioinspired synthesis cascade reactions [3+2] cycloaddition |
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