34 dl-Epiibogamineの全合成

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概要

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• The total synthesis of dl-ibogamine (Ia) and dl-ibogaine (Ic), the representative members of these alkaloids, and of the corresponding C-4 epimers were already achived by Buchi, Nagata, Kutney and Sallay, independently. The syntheses of some derivatives having the isoquinuclidine ring system were also reported. In the preliminary experiments for the total synthesis of ibogaine, we reported the syntheses of the keto-ester (XI) and the dl-C_<nor>-C_<20>-hydroxyepiibogamine (Ie). In this communication, we describe the total synthesis of dl-epiibogamine (Ib). The ketal-ester (XIII) was transformed by the action of methylsulfinyl carbanion into the methylsulfinyl adduct, which without isolation, was immediately reduced with aluminum amalgam to the ketal-acetylderivative (XVI). The ethyl-ketal (XVII) obtained from XVI by the Huang-Minlon reduction was hydrolyzed with 10% hydrochloric acid to the desired ethyl-ketone (XVIII). Finally, the phenylhydrazone of XVIII was submitted to the Fischer indolization refluxing with anhydrous formic acid for a half hour to afford dl-epiibogamine (Ib) (m.p. 194-196) after purification by chromatography on alumina eluted with benzene-methylenchloride (1:1). The infrared spectrum of the present product was superimposable on that of the authentic sample kindly provided by Dr. W. Negata. The identity of both samples was further confirmed by the mixed melting point determination, Rf values on TLC and the mass spectral comparison.

• 天然有機化合物討論会の論文
• 1968-09-20

著者

• 池崎 宗克

  北大(薬)

• 藤本 康雄

  北大(薬)

• 若松 武

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 大石 武

  北大・薬:(現)理化学研究所

• 伴 義雄

  北大(薬)

• 若松 武

  北大(薬)

• 大石 武

  北大(薬)

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