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Total Syntheses of Complanadines A and B

Authors

  • Le Zhao,

    1. Department of Chemistry, Graduate School of Science, Tohoku University, 6–3 Aramaki Aza-Aoba, Aoba-ku, Sendai 980-8578 (Japan)
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  • Dr. Chihiro Tsukano,

    Corresponding author
    1. Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501 (Japan)
    • Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501 (Japan)
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  • Dr. Eunsang Kwon,

    1. Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, 6–3 Aramaki Aza-Aoba, Aoba-ku, Sendai, 980-8578 (Japan)
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  • Prof. Dr. Yoshiji Takemoto,

    1. Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501 (Japan)
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  • Prof. Dr. Masahiro Hirama

    1. Department of Chemistry, Graduate School of Science, Tohoku University, 6–3 Aramaki Aza-Aoba, Aoba-ku, Sendai 980-8578 (Japan)
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  • We gratefully thank Profs. J. Kobayashi, H. Morita, and T. Kubota for providing the natural products and 1H and 13C NMR spectra. This work was financially supported by a Grant-in-Aid for Scientific Research on Innovation Area “Molecular Activation Directed toward Straightforward Synthesis” from The Ministry of Education, Culture, Sports, Science and Technology (Japan) (C.T.).

Abstract

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Twice as nice: Total syntheses of dimeric alkaloids, (−)-complanadines A (1) and B (2), were achieved from (−)-lycodine. The unsymmetrical motif was assembled through direct arylation of the pyridine N-oxide. The absolute configuration and specific rotations of complanadines A and B were identified. Cbz=Benzyloxycarbonyl.

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