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Total Synthesis of the Tremorgenic Indole Diterpene Paspalinine

Authors

  • Dr. Masaru Enomoto,

    1. Bioproduction Research Institute, National Institute of Advanced Industrial Science and Technology, Sapporo 062-8517 (Japan)
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  • Dr. Akira Morita,

    1. Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University, Tsutsumidori-Amamiyamachi, Sendai 981-8555 (Japan)
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  • Prof. Dr. Shigefumi Kuwahara

    Corresponding author
    1. Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University, Tsutsumidori-Amamiyamachi, Sendai 981-8555 (Japan)
    • Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University, Tsutsumidori-Amamiyamachi, Sendai 981-8555 (Japan)
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  • We thank Prof. Hidetoshi Tokuyama (Tohoku University) for valuable discussions. Financial support for this work was provided by the Ministry of Education, Culture, Sports, Science, and Technology (Japan) (no. 23780112)

Abstract

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Succinct and stereoselective: A high-yielding two-step indole ring installation comprising the Stille cross-coupling and a PdII-mediated oxidative heterocyclization was exploited in a concise total synthesis of paspalinine. The trans-anti-trans CDE fused ring system of the heptacyclic natural product was established highly stereoselectively through hydroxy-directed cyclopropanation and allylic selenoxide rearrangement.

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