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A new approach to the bicyclo[3.3.1]nonane framework of huperzine A-like molecules via palladium-catalyzed intramolecular γ-arylation

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Abstract

In our synthetic studies toward huperzine A, a diastereoselective α′-alkylation of the α-amido-γ-methyl hexenone 4 was realized through a dianion intermediate which significantly enhanced the reactivity. Under the attempted Heck reaction conditions, an unexpected and unprecedented palladium-catalyzed intramolecular γ-arylation of 3 was observed, which generated 18 with bicyclo[3.3.1]nonane framework in satisfactory yield.

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Authors and Affiliations

  1. CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, CAS, Shanghai, 200032, China

    Rui Ding, YunYu Lu, BingFeng Sun & GuoQiang Lin

  2. Department of Medicinal Chemistry, School of Pharmacy, China Pharmaceutical University, Nanjing, 210009, China

    YunYu Lu & HeQuan Yao

Authors
  1. Rui Ding
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  2. YunYu Lu
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  3. HeQuan Yao
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  4. BingFeng Sun
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  5. GuoQiang Lin
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Correspondence to BingFeng Sun or GuoQiang Lin.

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Ding, R., Lu, Y., Yao, H. et al. A new approach to the bicyclo[3.3.1]nonane framework of huperzine A-like molecules via palladium-catalyzed intramolecular γ-arylation. Sci. China Chem. 55, 1097–1100 (2012). https://doi.org/10.1007/s11426-011-4480-y

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