【摘要】 目的寻求一种高效、低廉的半合成紫杉醇的途径。方法在可回收非支载型手性配体的催化作用下,通过不对称双羟化反应合成紫杉醇C13侧链,对侧链的羟基和氨基进行保护后生成(4S,5R)-N-苯甲酰基-2-(4′-甲氧基)苯基-4-苯基-1,3-氧氮杂戊环-5-甲酸,进而和7-三乙基硅烷巴卡亭-Ⅲ缩合、去保护获得紫杉醇。结果获得了高光学纯度的紫杉醇C13侧链(化学产率52%,光学纯度99%),紫杉醇的总产率为30%,光学纯度为99%。结论此方法反应步骤少、操作简单、成本低廉,为紫杉醇的半合成开辟了一条新路线。更多还原

【Abstract】 OBJECTIVE To synthesize the taxol by a new,economical and practical way.METHODS The C13 side chain of the taxol was synthesized via asymmetric dihydroxylation of trans-cinnamate,which was catalyzed by a kind of free recoverable and resued chiral ligand and OsO4.Then the-OH and-NH2 groups of the C13 side chain were protected and(4S,5R)-N-benzoyl-2-(4′-methoxy) phenyl-4-phenyl-1,3-oxazolidine-5-carboxylic acid was prepared.Finally,the taxol was generated by condensing(4S,5R)-N-benzoyl-2-(4′-methoxy) phenyl-4-phenyl-1,3-oxazolidine-5-carboxylicacid with 7-triethysilyl baccatin-Ⅲ,deprotection and purification.RESULTS The C13 side chain of the taxol was obtained with the chemical yield of 52% and e.e.of 99%.Total yield of taxol was 30%,and e.e.was 99%.CONCLUSION This method to synthesize taxol is so convenient and practical that it is possible to be of economic significance to produce taxol in a large scale.更多还原