33 ProtoberberineからBenzo〔c〕phenanthridine及び3-Arylisoquinolineアルカロイドの合成
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概要
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Benzo[c]phenanthridine alkaloids have been shown to be biosynthesized from the corresponding protoberberine alkaloids through oxidative C_6-N bond cleavage, followed by recyclization between C_6 and C_<13> position of the latter alkaloids via the hypothetical enamino-aldehyde (A). This enamino-aldehyde (A) has also supposed to be the key intermediate for biosynthesis of 3-arylisoquinoline alkaloids from protoberberine alkaloids. According to the above biogenetic process, we have accomplished a novel and efficient synthesis of dihydrosanguilutine (7) and sanguilutine (8), 2,3,7,8,10-pentaoxygenated benzo[c]phenanthridine alkaloids, and (±)-corydalic acid methyl ester (20), a representative 3-arylisoquinoline alkaloid. 2,3,9,10,12-Pentamethoxyprotoberberine (2) was converted to the enamide (4) through the Hofmann degradation. Oxidation of 4 with thallium trinitrate followed by acidic treatment afforded oxysanguilutine (6), reduction of which with LiAlH_4 and then with NaBH_4 provided dihydrosanguilutine (7). The Hofmann degradation of the N-methyl derivative (14), derived from corysamine (12C), gave the enamine (15), which was reduced with NaBH_3CN to yield the trans amine (16) as a major product. On sequential treatment with Tl(NO_3)_3, 5% HCl, Jones reagent, and diazomethane, the trans amine (16) afforded (±)-corydalic acid methyl ester (20). Furethermore we have developed a convenient method for a synthesis of 13-methylprotoberberine alkaloids (12) from protoberberines (9) through photo-induced electrocyclic reaction of the 13-methylene-8,14-cycloberbines (11), derived from 10 by the Wittig reaction.
- 天然有機化合物討論会の論文
- 1985-09-07
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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向 智里
金沢大・薬
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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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小林 伸行
金沢大・薬
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小林 伸行
Faculty Of Pharmaceutical Sciences Kanazawa University
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