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Acta Chimica Sinica ›› 1965, Vol. 31 ›› Issue (6): 470-475. Previous Articles Next Articles
黄文魁, 張振杰, 林根寿
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HWANG WEN-KUEI, CHANG CHENG-CHIEH, LIN GENG-SHOU
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Both natural l-a-narcotise (Ⅰ) and artificial l-β-narcotise(Ⅱ) were reduced by LiAlH4 to the α-diol (Ⅲ),m.p. 132°, [α]D15+51.2° (CHCl3),Al2O3 thin layer chromato-graphy Rf 0.63 (ether),and the β-diol (IV), m.p. 60-61°,[α]D15-59.5° (CHCl3),Al2O3 thin layer chromatography Rf 0.45 (ether),respectively. The latter was contaminated with a small amount of a-diol (Ⅲ),the yield of which was increased to 32% as the reaction time is prolonged to four hours. A copper complex (Ⅴ') could be prepared from the,β-diol (Ⅳ),but not from the a-diol (Ⅲ).From these facts, the relafive configurations of both l-α-narcotise (Ⅰ) and l-β-narcotise (Ⅱ) should be referred to as belonging to the erythro-and threo-series, respectively.
HWANG WEN-KUEI, CHANG CHENG-CHIEH, LIN GENG-SHOU. STEREOCHEMISTRY OF NARCOTINE AND RELATED ALKALOIDS[J]. Acta Chimica Sinica, 1965, 31(6): 470-475.
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