64 ProtoberberineアルカロイドからBenzo [c] phenanthridineアルカロイドの生合成的合成(口頭発表の部)
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概要
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Benzo[c]phenanthridine alkaloids have been shown to be biosynthesized from the corresponding alkaloids through an oxidative C_6-N bond cleavage followed by recyclization between C_6 and C_<13> position of the latter alkaloids via the hypothetical aldehydeemamines. And a hexa-oxygenated fully aromatized alkaloid has been found to be biosynthesized from a 2,3,7,8-tetra-oxygenated one through a penta-oxygenated one. According to the above biosynthetic process, we have accomplished a novel and efficient synthesis of penta-oxygenated benzo[c]phenanthridine alkaloids, chelirubine (7), chelilutine (13a) and sanguilutine (13b), and macarpine (20), a hexaoxygenated one, and B/C-hexahydrobenzo[c]phenanthridine alkaloids, (±)-corynoline (27), (±)-11-epicorynoline (28), (±)-isocorynoline (29), and (±)-11-epiioscorynoline (30). Dihydrofagaridine (10a) and its analogue (10b), derived from palmatine (8b) were converted to chelilutine (13a) and sanguilutine (13b), respectively, through salcomine-catalyzed oxidation and reductive methylation. Oxychelirubine (5) was converted to oxymacarpine (18) through regioselective iodination followed by methoxylation with NaOMe in the presence of CuI and CuO. Oxymacarpine was derived to dihydromacarpine (19) and macarpine (20). Sequential treatment of the Hofmann degradation product (23), devived from corysamine (21), with Tl(NO_3)_3, NaBH_4, 15% HCl, and NaBH_3CN afforded (±)-corynoline (27) along with (±)-11-epicorynoline (28). Reduction with zinc instead of NaBH_3CN in the above reaction gave (±)-isocorynoline (29) accompanied with (±)-11-epiisocorynoline (30), 27, and 28.
- 天然有機化合物討論会の論文
- 1988-09-26
著者
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花岡 美代次
金沢大学薬学部
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向 智里
金沢大学薬学部
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花岡 美代次
金沢大・薬
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趙 元済
金沢大・薬
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向 智里
金沢大・薬
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趙 元済
Faculty of Pharmaceutical Sciences, Kanazawa University
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趙 元済
Faculty Of Pharmaceutical Sciences Kanazawa University
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吉田 修治
Faculty Of Pharmaceutical Sciences Kanazawa University
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吉田 修治
金沢大・薬
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花岡 美代次
Institute Of Natural Medicine University Of Toyama
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