Development of Unprotected Syntheses in Aqueous Media

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  • 水を溶媒とした無保護合成反応の開発
  • ミズ オ ヨウバイ ト シタ ムホゴ ゴウセイ ハンノウ ノ カイハツ

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Introduction of carbon side chain at C3-position of indole ring was accomplished by using Pd-catalyzed allylation and vinylation. The selective vinylation at C3-position of 4-bromoindole was applied to the synthesis of optically active 4-bromotryptophan derivatives, which was used as a starting material for the synthesis of several optically active ergot alkaloids, which were clavicipitic acids, chanoclavine-I, costacalvine, and 1,1-dimethylallyltryptophan (DMAT). The three-step synthesis of optically active clavicipitic acids were accomplished without using a protecting group starting from 4-bromoindole and dl-serine. Some new synthetic reactions using unprotected amino acids were developed. Those were the biomimetic synthesis of tryptophan, the bromination of free aromatic amino acids, and the Pd-catalyzed N-allylation of free amino acids with allylic alcohol in aqueous media. Unique reactivity of π-allyl palladium complex or η3-(benzyl)palladium complex in aqueous media was found through Pd-catalyzed reaction of anthranilic acid, 2-aminobenzamide, and indole with allylic alcohols or benzyl alcohols, respectively.<br>

Journal

  • YAKUGAKU ZASSHI

    YAKUGAKU ZASSHI 133 (2), 249-268, 2013-02-01

    The Pharmaceutical Society of Japan

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