58 ProtoberberineアルカロイドからBenzo[c]phenanthridineアルカロイドの高立体選択的合成
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概要
- 論文の詳細を見る
Benzo[c]phenanthridine alkaloids have been shown to be biosynthesized from the corresponding protoberberine alkaloids through an oxidative C_6-N bond cleavage, followed by recyclization between C_6 and C_<13> position of the latter. On the basis of this biogenetic route, we have accomplished a highly stereoselective synthesis of (±)-chelamidine (7a), (±)-chelamine (7b), (±)-homochelidonine (8a), and (±)-chelidonine (8b) via the key intermediate (6) which has also provided fully aromatized benzo[c]phenanthridine alkaloids, chelerythrine (9a), dihydrochelerythrine (10a), sanguinarine (9b), and dihydrosanguinarine (10b). Berberine (1a) and coptisine (1b) were converted to the alcohols (4 and 5) through successive the Hofmann degradation, oxidation, and reduction. On exposure to concentrated sulfuric acid in acetic acid, the alcohols (4 and 5) underwent cationic cyclization to furnish the key and common intermediate (6). Stereoselective introduction of oxygen function at C_<11> and C_<12> position in 6 was realized by oxidation with performic acid to yield (±)-chelamidine (7a) and (±)-chelamine (7b), both of which were converted into (±)-homochelidonine (8a) and (±)-chelidonine (8b), respectively. The benzo[c]phenanthridine (6) was also dehydrogenated with Pd-C to give chelerythrine (9a), dihydro-chelerythrine (10a), sanguinarine (9b), and dihydrosanguinarine (10b).
- 天然有機化合物討論会の論文
- 1986-09-09
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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