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Catalytic Asymmetric Total Synthesis of Chimonanthine, Folicanthine, and Calycanthine through Double Michael Reaction of Bisoxindole

Authors

  • Harunobu Mitsunuma,

    1. Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
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  • Prof. Dr. Masakatsu Shibasaki,

    1. Institute of Microbial Chemistry, Tokyo, Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan)
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  • Prof. Dr. Motomu Kanai,

    Corresponding author
    1. Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
    2. Kanai Life Science Catalysis Project, ERATO (Japan) Science and Technology Agency, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
    • Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
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  • Dr. Shigeki Matsunaga

    Corresponding author
    1. Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
    2. Kanai Life Science Catalysis Project, ERATO (Japan) Science and Technology Agency, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
    • Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan)
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  • We thank Prof. Kobayashi, Prof. Ohwada, Dr. Otani, and Dr. Ueno at the University of Tokyo for generous technical supports. This work was supported by Scientific Research on Innovative Areas from MEXT, ERATO from JST, Grant-in-Aid for Young Scientists (A) from JSPS, Inoue Science Foundation, and Takeda Science Foundation.

Abstract

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Direct access: Sterically hindered vicinal quaternary carbon stereocenters were constructed by catalytic enantio- and diastereoselective double Michael reaction, providing straightforward access to dimeric hexahydropyrroloindole alkaloids. A Mn(4-fluorobenzoate)2/Schiff base complex and a Mg(OAc)2/benzoic acid system were used as catalysts.

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