麦角アルカロイド化合物群を対象とする究極の合成を目指して

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書誌事項

タイトル別名
  • Studies Directed toward the Ultimate Synthesis for Ergot Alkaloids
  • バッカク アルカロイド カゴウブツグン オ タイショウ ト スル キュウキョク

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抄録

The ultimate synthesis is defined as an ideal one step synthesis satisfying the first to the third element of our synthetic philosophy as shown in Fig. 1. The fourth element is a necessary process for accessing to the ultimate synthesis. One pot synthesis is the second best. In our continuing studies directed toward the ultimate synthesis for ergot alkaloids, simple and practical methods for the preparation of various 4-substituted indoles were elaborated starting from indole-3-carboxaldehyde (1). A common synthetic method, shown in Chart 4, was also elaborated and total syntheses of (±)-6, 7-secoagroclavine, (±)-isochanoclavine-I and II, (±)-norchanoclavine-I, (±)-chanoclavine-I and II, (±)-isochanoclavine-I and II, (±)-agroclavine, (±)-agroclavine-I, and (±)-aurantioclavine were achieved by changing only olefin component at the second step with the same common procedures for other steps. Basic concept of thallation-palladation reaction (in the broad sense) is illustrated and in the process of its generalization, thallation-palladation (in the narrow sense), boronation-thallation, and tin-thall reactions were discovered as desired new cross coupling reactions which work directly at the 4-position of the indole nucleus. By employing tin-thall reaction, 4-(3-pyridyl)indole-3-carboxaldehyde (104) and methyl 5-(3-formylindol-4-yl)nicotinate (120) become readily available in one pot operation from 1.

収録刊行物

  • 薬学雑誌

    薬学雑誌 108 (5), 361-380, 1988

    公益社団法人 日本薬学会

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