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Total Synthesis of Hapalindole-Type Natural Products†

Authors

  • Zhaohong Lu,

    1. State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China)
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    • These authors contributed equally to this work.

  • Ming Yang,

    1. State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China)
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    • These authors contributed equally to this work.

  • Pengxi Chen,

    1. State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China)
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  • Xiaochun Xiong,

    1. State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China)
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  • Prof. Dr. Ang Li

    Corresponding author
    1. State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China)

    • State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China)

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  • †

    This work was supported by the Ministry of Science & Technology (2013CB836900), the National Natural Science Foundation of China (21290180, 21172235, and 21222202), the Pujiang Program (12J1410800), and the China Postdoctoral Science Foundation (2014M551480 to M.Y.).

Abstract

A unified and bioinspired oxidative cyclization strategy was used in the first total syntheses of naturally occurring 12-epi-hapalindole Q isonitrile, hapalonamide H, deschloro 12-epi-fischerindole I nitrile, and deschloro 12-epi-fischerindole W nitrile, as well as the structural revision of the latter. Hapalindoles H and Q were also synthesized.

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Article Information

DOI

10.1002/anie.201406626

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© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

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Keywords

  • hapalindole;
  • indole terpenoids;
  • Prins cyclization

Publication History

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  • Version of record online:
  • Manuscript Received:

Funded by

  • Ministry of Science & Technology. Grant Number: 2013CB836900
  • National Natural Science Foundation of China. Grant Numbers: 21290180, 21172235, 21222202
  • Pujiang Program. Grant Number: 12J1410800
  • China Postdoctoral Science Foundation. Grant Number: 2014M551480

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