New, Concise Route to Indoles Bearing Oxygen or Sulfur Substituent at the 4-Position. Synthesis of (±)- and (S)-(-)-Pindolol and (±)-Chuangxinmycin
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概要
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A new method for the synthesis of 4-alkoxy- and 4-[alkyl (or aryl)thio]indoles has been developed by using the indolone 3 as a common intermediate. The indolone 3 was prepared from N-(phenylsulfonyl)pyrrole (7) and the α-chlorosulfide 8 in four steps. Heating of a mixture of 3 and an appropriate alcohol in the presence of p-toluenesulfonic acid and cupric chloride afforded the 4-alkoxyindoles 11a-d. The method was applied to the synthesis of (±)-pindolol (19) and (S)-(-)-pindolol (20). Thiols also reacted with 3 in the presence of boron trifluoride to give 4-[aryl (or alkyl)thio]indoles 12,21a, b, and 22a-d. The (indol-4-ylthio)acetate 22c was employed as a key intermediate for a concise total synthesis of (±)-chuangxinmycin (27).
- 社団法人日本薬学会の論文
- 1994-02-15
著者
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池田 正澄
Kyoto Pharmaceutical University
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池田 正澄
京都薬科大学
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石橋 弘行
Kyoto Pharmaceutical University
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石橋 弘行
金沢大学薬学部
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石橋 弘行
京都薬科大学
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赤松 進
Kyoto Pharmaceutical University
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入山 浩子
Kyoto Pharmaceutical University
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花岡 恭子
Kyoto Pharmaceutical University
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田畑 隆志
Kyoto Pharmaceutical University
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