Synthesis of Indole Compounds Using Multifunctional Synthons

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  • Abe Takumi
    Faculty of Pharmaceutical Sciences, Health Science University of Hokkaido

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  • 多官能性合成素子を用いるインドール化合物の合成
  • タカンノウセイ ゴウセイ ソシ オ モチイル インドール カゴウブツ ノ ゴウセイ

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Abstract

  This review describes a synthesis of indole compounds using multifunctional synthons. The multifunctional synthons, trienes and gramines, were respectively synthesized using Pd-catalyzed tandem cyclization/cross-coupling reaction of indolylborate with vinyl bromide, and reaction of indolylcuprate with iminium chloride. As an application of the multifunctional synthons to the indole alkaloids synthesis, we accomplished the total synthesis of ellipticine, 9-methoxyellipticine, 9-hydroxyellipticine, tetrahydroellipticine, μ-alkaloid B, μ-alkaloid D, calothrixin A, calothrixin B, tubifoline, and yuehchukene. We have also developed 6π-electrocyclization of hexatrienes catalyzed by Cu(I) trifluoromethanesulfonate toluene complexe, which is unprecedented.<br>

Journal

  • YAKUGAKU ZASSHI

    YAKUGAKU ZASSHI 133 (1), 99-106, 2013-01-01

    The Pharmaceutical Society of Japan

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