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《Journal of Zhejiang University(Engineering Science)》 2006-03
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Research on total synthesis of racemic galanthamine

LIU Tao,QIAN Chao,CHEN Xin-zhi(College of Materials Science and Chemical Engineering,Zhejiang Univercity,Hangzhou 310027,China)  
Considering the problem of total synthesis of galanthamine,a new technology of total synthesis of the racemic galanthamine was put forward.Using isovanillin and tyramine as the initial materials,racemic galanthamine was prepared in five steps including bromination,condensation and reduction,formylation, oxidation coupling and reduction.The title compound and the key intermediates were characterized by high performance liquid chromatography(HPLC),infrared spectrum(IR),mass spectrum(MS) and nuclear magnetic resonance(NMR).The effects of temperature,catalyst and solvent on cell reaction were studied.The results show that Bromination in methanol has the yield of 85.5% at-60~-65℃.The yield of condensation is 91.2% with SSY molecular sieve as catalyst and NaBH_4 as reducing agent.The yield of formylation is 80.0%.The yield of oxidation phenolic coupling by K_3[Fe(CN)_6] is 46.1%.The yield of reduction is 83.0% with LiAlH_4 as reducing agent.
【CateGory Index】: TQ463
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