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Total Synthesis of (−)-13-Oxyingenol and its Natural Derivative

Authors

  • Dr. Takayuki Ohyoshi,

    1. Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8571 (Japan)
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    • Research fellow of the Japan Society for the Promotion of Science (JSPS).

  • Shota Funakubo,

    1. Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8571 (Japan)
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  • Yamato Miyazawa,

    1. Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8571 (Japan)
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  • Keisuke Niida,

    1. Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8571 (Japan)
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  • Dr. Ichiro Hayakawa,

    1. Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8571 (Japan)
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  • Prof. Dr. Hideo Kigoshi

    Corresponding author
    1. Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8571 (Japan)
    • Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8571 (Japan)
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  • This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science, and Technology (MEXT; Japan); by a grant from the Uehara Memorial Foundation, and by a grant from the Suntory Institute for Bioorganic Research (SUNBOR GRANT). We thank the Takasago International Corp. for their gift of (S)-β-hydroxy γ-butyrolactone. We would also like to thank Prof. Daisuke Uemura (Kanagawa University) for providing a sample of the 13-oxyingenol derivative and for his helpful discussion.

Abstract

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Ring functionalization: The total synthesis of a natural derivative of (−)-13-oxyingenol, a potent anti-HIV diterpenoid, is reported. The key steps in this synthesis include a ring-closing olefin metathesis and a Mislow–Evans-type [2,3]-sigmatropic rearrangement. This synthesis provides access to (−)-13-oxyingenol and its natural derivative in 21 steps from a synthetic intermediate previously prepared by Kigoshi and co-workers.

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