Constituents of Rhizoma Nupharis. XVIII. Synthesis of Alkaloids from Nuphar japonicum DC. I. Synthesis of rac-Deoxynupharidine.

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概要

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• Condensation of octahydro-4-quinolizinone (I) and ethyl 3-furoate affords (II) which, on being heated with dilute hydrochloric acid, forms a compound (IV) of hexahydro-quinolizine series. Reduction of (IV) with sodium borohydride gives (V) which is separated into two kinds of racemate showing infrared absorption band due to trans-quinolizidine. By the route shown above, (XVII) was obtained from 1,7-dimethyloctahydro-4-quinolizinone (XII) and (XVII) was separated into three kinds of bases. From the result of infrared spectral measurement, (XVIIa) and (XVIIc) were assumed to be trans-quinolizidine compound and (XVIIb) was assumed to be cis-quinolizidine compound. The infrared spctra (in carbon tetrachloride solution) of (XVIIa) and (-)-deoxynupharidine isolated from Nuphar japonicum DC. were found to be entirely identical and (XVIIa) was concluded to be rac-deoxynupharidine.

• 社団法人日本薬学会の論文
• 1962-08-25

著者

• 荒田 義雄

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 中西 外志子

  Faculty of Pharmacy, Kanazawa University

• 浅岡 陽子

  Faculty of Pharmacy, Kanazawa University

• 浅岡 陽子

  Faculty Of Pharmacy Kanazawa University

• 中西 外志子

  Faculty Of Pharmacy Kanazawa University

• 荒田 義雄

  Faculty of Pharmaceutical Sciences, Kanazawa University

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