Total Syntheses of Lactonamycin and Lactonamycin Z with Late-Stage A-Ring Formation and Glycosylation

Authors

  • Satoshi Adachi,

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

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

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

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

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

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

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

    Corresponding author
    1. Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522 (Japan)
    • Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522 (Japan)
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  • Prof. Dr. Masaya Nakata

    Corresponding author
    1. Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522 (Japan)
    • Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama 223-8522 (Japan)
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  • We thank the Institute of Microbial Chemistry, Microbial Chemistry Research Foundation for providing us with natural lactonamycin. We are also grateful to Emeritus Professors Hans-Peter Fiedler (Universität Tübingen), for providing us natural lactonamycin Z, and Ronald Parry (Rice University), for the discussion about the absolute configuration of lactonamycin Z. This research was partially supported by a “MEXT-Supported Program for the Strategic Research Foundation at Private Universities 2012-2016”.

Abstract

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The highly oxygenated polyketide antibiotics, lactonamycin and lactonamycin Z were synthesized. The BCDEF ring system was constructed by a cycloaddition and a palladium-catalyzed cyclization and a Bischler–Napieralski-type cyclization was used for the formation of the A ring. The glycosylation of the aglycon with the appropriate sugar gave lactonamycin and lactonamycin Z.

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