Total Synthesis of the Alkaloid (±)-Dendrobine

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概要

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• Total synthesis of (±)-dendrobine has been completed. The ketol (19) was derived to the keto-nitrile (21). Hydrogenation of (21) gave the compound (5). Treatment of (5) with Br_2,followed by dehydrobromination provided the enone (6). After ketalization, the compound (5) was hydrolyzed and deketalization of the product gave the keto-lactone (8). The compound (8) was derived to the keto-lactam (9) which was successively treated with iso-PrMgBr, KHSO_4,I_2-AcOAg-AcOH-H_2O, KOH-MeOH-H_2O, and CrO_3-pyridine to afford the enone (10) and (55). Hydrocyanation of (10) with Et_2AlCN gave three isomeric cyano-ketones (11), (56), and (57). Hydrolysis of the cyano-ketone (11) with H_2SO_4-AcOH, followed by methylation afforded the keto-ester (60). Reduction of (60) with NaBH_4 gave the hydroxy-ester (61). Hydrolysis of (61) with KOH, followed by acidification yielded (±)-oxodendrobine (13). Reduction of (13) by the Borch's method gave (±)-dendrobine (1).

• 公益社団法人日本薬学会の論文
• 1974-02-25

著者

• 犬伏 康夫

  Faculty of Pharmaceutical Sciences, Kyoto University

• 井深 俊郎

  Faculty of Pharmaceutical Sciences, Kyoto University

• 田中 圭

  Faculty Of Pharmaceutical Sciences Kyoto University

• 田中 圭

  静岡県大 薬

• 菊池 徹

  Faculty of Pharmaceutical Sciences, Kyoto University

• 井深 俊郎

  Faculty Of Pharmaceutical Sciences Kyoto University

• 菊池 徹

  Faculty Of Pharmaceutical Sciences Kyoto University

• 佐治 幾太郎

  京大・薬

• 犬伏 康夫

  Faculty Of Pharmaceutical Sciences Kyoto University

• 佐治 幾太郎

  Faculty of Pharmaceutical Sciences, Kyoto University

• 兜金 和夫

  Faculty of Pharmaceutical Sciences, Kyoto University

• 田中 圭

  京都大学薬学部

• 兜金 和夫

  Faculty Of Pharmaceutical Sciences Kyoto University

• 田中 圭

  Faculty of Eng., Oita Univ.

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