Transformation of Indole Alkaloids. VI. A Novel Conversion of Oxindole Alkaloids into Indole Alkaloids via Indoline Derivatives

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概要

• 論文の詳細を見る

• Oxindole alkaloids chosen as starting materials were isopteropodine (1a) pteropodine (1b) isoformosanine (7a) and formosanine (7b). Reduction of the iminoethers prepared from the oxindole alkaloids with Et_3 O^^+B^^-F_4,with NaBH_3 (OAc) or with NaBH_4/SnCl_4・2Et_2O afforded the indoline derivatives (3a, 3b, 9a, 9b). The configuration at C_7 of 3a, b was determined by NMR analysis of the N (a)-acetyl-N (b)-oxides (6a, b). The signals of H-14β were observed at high field (δ0.5-1.0) owing to the shielding effect of the aromatic ring in all A type compounds studied. Oxidative conversion of the indolines to indole alkaloids was achieved by using MnO_2 or Me_2SO/ (COCl)_2/Et_2N as oxidizing agents, and the latter reagent gave better results than the former. Tetrahydroalstonine (11) and akuammigine (12) were obtained from 3a, b, and 19-epiajmalicine (14) and 3-iso-19-epiajmalicine (15) from 9a, b. The A type compounds were more susceptible than the B type compounds to the present reduction and oxidation sequence.

• 公益社団法人日本薬学会の論文
• 1982-06-25

著者

• 坂井 進一郎

  Faculty of Pharmaceutical Sciences, Chiba University

• 山中 悦二

  Department Of Medicinal Materials:faculty Of Pharmaceutical Sciences Chiba University

• 山中 悦二

  Faculty of Pharmaceutical Sciences, Chiba University

• 斉藤 直樹

  Faculty of Pharmaceutical Sciences, Chiba University

• 鈴木 優子

  Faculty of Pharmaceutical Sciences, Chiba University

• 斉藤 直樹

  Faculty Of Pharmaceutical Sciences Chiba University

• 鈴木 優子

  Faculty Of Pharmaceutical Sciences Chiba University

• 坂井 進一郎

  Faculty Of Pharmaceutical Sciences Chiba University

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