Total Synthesis of (±)-Kopsihainanine A

Authors

  • Peng Jing,

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu, 730000 (P.R. China), Fax: (+86) 931-8912582
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  • Zhen Yang,

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu, 730000 (P.R. China), Fax: (+86) 931-8912582
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  • Changgui Zhao,

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu, 730000 (P.R. China), Fax: (+86) 931-8912582
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  • Huaiji Zheng,

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu, 730000 (P.R. China), Fax: (+86) 931-8912582
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  • Bowen Fang,

    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu, 730000 (P.R. China), Fax: (+86) 931-8912582
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  • Dr. Xingang Xie,

    Corresponding author
    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu, 730000 (P.R. China), Fax: (+86) 931-8912582
    • State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu, 730000 (P.R. China), Fax: (+86) 931-8912582
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  • Prof. Dr. Xuegong She

    Corresponding author
    1. State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu, 730000 (P.R. China), Fax: (+86) 931-8912582
    2. State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, Gansu, 730000 (P.R. China)
    • State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu, 730000 (P.R. China), Fax: (+86) 931-8912582
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Abstract

original image

Going all the way: The first total synthesis of (±)-kopsihainanine A has been achieved in ten steps with a 12 % overall yield from commercially available 1,2,3,4-tetrahydrocarbazol-4-one (see scheme). This synthesis features an intramolecular conjugate addition of the iminium ion formed in situ with the amide and a substrate-controlled diastereoselective α-hydroxylation. Furthermore, ring D is formed by a late-stage transannular SN2 reaction.

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