54 8,14-Cycloberbineを経由するProtoberberineアルカロイドからSpirobenzylisoquinoline及びBenzindenoazepineアルカロイドの合成
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概要
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Stereoselective total syntheses of spirobenzylisoquinoline alkaloid (±)-ochrobirine and benzindenoazepine alkaloids fumarofine, O-methylfumarofine, and (±)-fumaritrine were accomplished from biogenetic precursors, protoberberines via 8,14-cycloberbines. 1. Synthesis of Spirobenzylisoquinoline Alkaloid (±)-Ochrobirine Stereoselective reduction of the cycloberbine (14) derived from coptisine (12) with LiAlH(OBu^t)_3, followed by treatment with ClCO_2Et gave the oxazolidinone (17). Alkaline hydrolysis of 17 and subsequent methylation with MeI afforded (±)-ochrobirine (6). 2. Synthesis of Benzindenoazepine Alkaloids Fumarofine and O-Methyl-fumarofine Regioselective C_<14>-N bond cleavage of the cycloberbine (24) derived from the protoberberine (22) with MeSO_3H afforded benzindenoazepines (25 and 26) which were treated with MeI to give cis N-methylazepine (27). Hydrogenolysis of 27 furnished fumarofine (19), O-methylation of which gave O-methylfumarofine (20). 3. Synthesis of Benzindenoazepine Alkaloid (±)-Fumaritrine Sodium borohydride reduction of the cycloberbine (37) derived from dihydroepiberberine (35) afforded stereoselectively the alcohol (38), which was treated with p-TsOH in MeOH to give stereoselectively the cis methoxy-azepine (39). Its N-methyl derivative (40) was mesylated and followed by reduction with NaBH_4 to give (±)-fumaritrine (28).
- 天然有機化合物討論会の論文
- 1983-09-15
著者
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桜井 俊一郎
北陸製薬株式会社中央研究所研究開発本部
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山岸 喬
Natural Products Laboratory Division Of Medicinal Chemistry And Natural Products School Of Pharmacy
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山岸 浩
Faculty Of Pharmaceutical Sciences Kanazawa University
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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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向 智里
金沢大薬
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花岡 美代次
金沢大薬
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安田 信吾
金沢大・薬
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桜井 俊一郎
金沢大薬
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足森 厚之
金沢大薬
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山岸 浩
金沢大薬
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岩崎 政司
金沢大薬
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安田 信吾
金沢大薬
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