Constituents of Rhizoma Nupharis. XXVIII. New Syntheses of (±)-7-Epideoxynupharidine, (±)-1-Epi-7-epideoxynupharidine, (±)-Deoxynupharidine, and (±)-1-Epideoxynupharidine

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概要

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• A new stereoselective synthesis of (±)-7-epideoxynupharidine (1), the most stable quinolizidine-type Nuphar alkaloid, is described. Condensation of 2-ethyl-5-methylpyridine (5) with acetonitrile, followed by ketalization, gave the ketal (13), which was hydrogenated to afford the piperidine (14). Deketalization of 14 afforded the aminoketone (15). Condensation of 15 with 3-furylaldehyde afforded four quinolizidin-2-ones (8,16,17,and 18) in 14,45,1,and 3% yields, respectively. The cis-quinolizidines (16 and 18) were isomerized to the trans-quinolizidines (8 and 17,respectively). Wolff-Kishner reduction of 8 afforded (±)-7-epideoxynupharidine (1) (45%) and (±)-1-epi-7-epideoxynupharidine (2) (15%). Similar reduction of 17 provided (±)-deoxynupharidine (3) (33%) and (±)-1-epideoxynupharidine (4) (14%).

• 公益社団法人日本薬学会の論文
• 1980-03-25

著者

• 荒田 義雄

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 花岡 美代次

  Faculty Of Pharmaceutical Sciences Osaka University

• 花岡 美代次

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 安田 信吾

  金沢大・薬

• 安田 信吾

  Faculty of Pharmaceutical Sciences, Kanazawa University

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