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Synthesis, Characterization, and Crystal Structure of a Phenanthroindolizine Skeleton from 18-Acetamino-7-Oxo-Dehydroabietane by Vilsmeier-Haack Reaction

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Chemistry of Natural Compounds Aims and scope

A facile and efficient one-step synthesis of a novel phenanthroindolizine skeleton was developed via the Vilsmeier–Haack reaction of accessible 18-acetamino-7-oxo-dehydroabietane. The structure and stereochemistry were confirmed by NMR, HR-MS, elemental analysis, and X-ray crystal structure analysis (XSA), and the proposed reaction pathway for the Vilsmeier-Haack reaction includes an unusual conjugate addition of enol to chloromethyleneiminium salt and intramolecular cyclization reaction.

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Acknowledgment

The generous financial support of the Natural Science Foundation of China (31170536) is gratefully acknowledged. This project was funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions.

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Authors and Affiliations

  1. College of Chemical Engineering, Nanjing Forestry University, 210037, Nanjing, P. R. China

    Chaoxiang Liu, Junqiang Hu, Haijun Xu, Zhou Lu, Xing Yu & Zhongxiang Lin

  2. Bozhou Vocational and Technical College, 236800, Bozhou, P. R. China

    Chaoxiang Liu

Authors
  1. Chaoxiang Liu
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  2. Junqiang Hu
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  3. Haijun Xu
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  4. Zhou Lu
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  5. Xing Yu
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  6. Zhongxiang Lin
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Corresponding authors

Correspondence to Haijun Xu or Zhongxiang Lin.

Additional information

Published in Khimiya Prirodnykh Soedinenii, No. 2, March–April, 2015, pp. 269–272.

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Liu, C., Hu, J., Xu, H. et al. Synthesis, Characterization, and Crystal Structure of a Phenanthroindolizine Skeleton from 18-Acetamino-7-Oxo-Dehydroabietane by Vilsmeier-Haack Reaction. Chem Nat Compd 51, 306–310 (2015). https://doi.org/10.1007/s10600-015-1266-z

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  • DOI: https://doi.org/10.1007/s10600-015-1266-z

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