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Total Synthesis and Absolute Stereochemistry of Seragakinone A

Authors

  • Akiomi Takada,

    1. Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551 (Japan), Fax: (+81) 3-5734-2788
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  • Yoshimitsu Hashimoto,

    1. Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551 (Japan), Fax: (+81) 3-5734-2788
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  • Dr. Hiroshi Takikawa,

    1. Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551 (Japan), Fax: (+81) 3-5734-2788
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  • Katsuyoshi Hikita,

    1. Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551 (Japan), Fax: (+81) 3-5734-2788
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  • Prof. Dr. Keisuke Suzuki

    Corresponding author
    1. Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551 (Japan), Fax: (+81) 3-5734-2788
    • Department of Chemistry, Tokyo Institute of Technology, 2-12-1 O-okayama, Meguro-ku, Tokyo 152-8551 (Japan), Fax: (+81) 3-5734-2788
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  • We thank Prof. Dr. Jun′ichi Kobayashi (Hokkaido Univ.) and Prof. Dr. Hideyuki Shigemori (Tsukuba Univ.) for kindly providing a comparison sample of 1. We are grateful to Sachiyo Kubo for X-ray analysis, and Dr. Haruko Takahashi for HSCCC purification.

Abstract

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Cyclic transformation: The key transformations of the asymmetric total synthesis of the marine-derived natural product seragakinone A are two N-heterocyclic carbene catalyzed benzoin cyclizations that result in the construction of two rings and a pinacol-type rearrangement to install the angular prenyl substituent.

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