Total Syntheses of Amphidinolides B, G, and H

Authors

  • Akihiro Hara,

    1. Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522 (Japan)
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  • Ryo Morimoto,

    1. Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522 (Japan)
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  • Yuki Iwasaki,

    1. Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522 (Japan)
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  • Dr. Tsuyoshi Saitoh,

    1. Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522 (Japan)
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  • Dr. Yuichi Ishikawa,

    1. Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522 (Japan)
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  • Prof. Dr. Shigeru Nishiyama

    Corresponding author
    1. Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522 (Japan)
    • Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522 (Japan)
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  • This work was financially supported by The Science Research Promotion Fund from The Promotion and Mutual Aid Corporation for Private Schools of Japan from MEXT. A.H. was indebted to the Sasagawa Foundation. We thank Prof. Dr. J. Kobayashi and Prof. Dr. T. Kubota (University of Hokkaido) for a gift of their spectral data. We are also grateful to T. Wakamatsu and K. Kariya for technical assistance.

Abstract

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Not one, not two, but three: Total syntheses of amphidinolides B, G, and H, which exhibit strong, nanogram-scale cytotoxicity against various tumor cell lines, have been executed. The synthetic strategy relied on implementation of a diene construction protocol and a diastereoselective aldol process. The 26- and 27-membered macrocyclic lactone rings were efficiently constructed by using ring-closing metathesis (RCM).

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