Epothilone D合成路线 (共 263 条)
反应条件
1.1: 2,6-dimethylpyridine / dichloromethane / 4 h / 0 - 5 °C 1.2: 3 h / 5 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C 3.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 3.2: 10.33 h / 20 °C 4.1: trifluoroacetic acid / dichloromethane / 1 h / -20 - 0 °C View Scheme
参考文献
Russian Journal of Organic Chemistry, , vol. 47, # 11 p. 1653 - 1674
反应条件
1.1: triethylamine / diethyl ether / 0 °C 2.1: magnesium; ethylene dibromide / diethyl ether / 0.37 h / 20 °C / Cooling 2.2: 0.53 h / 20 °C 2.3: 14 h / 20 °C 3.1: pyridinium p-toluenesulfonate; dimethyl sulfoxide / 4 h / 65 °C 4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C 4.2: -78 - 0 °C 5.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.75 h / -78 - 40 °C 5.2: 0.08 h / -78 °C 6.1: formic acid / diethyl ether / 10 h / 5 - 20 °C 7.1: [bis(acetoxy)iodo]benzene; water / tetrahydrofuran / 0.67 h / 20 °C 8.1: 2,6-dimethylpyridine / dichloromethane / 4 h / 0 - 5 °C 8.2: 3 h / 5 °C 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C 10.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 10.2: 10.33 h / 20 °C 11.1: trifluoroacetic acid / dichloromethane / 1 h / -20 - 0 °C View Scheme
参考文献
Russian Journal of Organic Chemistry, , vol. 47, # 11 p. 1653 - 1674
反应条件
1.1: magnesium; ethylene dibromide / diethyl ether / 0.37 h / 20 °C / Cooling 1.2: 0.53 h / 20 °C 1.3: 14 h / 20 °C 2.1: pyridinium p-toluenesulfonate; dimethyl sulfoxide / 4 h / 65 °C 3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C 3.2: -78 - 0 °C 4.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.75 h / -78 - 40 °C 4.2: 0.08 h / -78 °C 5.1: formic acid / diethyl ether / 10 h / 5 - 20 °C 6.1: [bis(acetoxy)iodo]benzene; water / tetrahydrofuran / 0.67 h / 20 °C 7.1: 2,6-dimethylpyridine / dichloromethane / 4 h / 0 - 5 °C 7.2: 3 h / 5 °C 8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C 9.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 9.2: 10.33 h / 20 °C 10.1: trifluoroacetic acid / dichloromethane / 1 h / -20 - 0 °C View Scheme
参考文献
Russian Journal of Organic Chemistry, , vol. 47, # 11 p. 1653 - 1674
反应条件
1.1: pyridine; 4-(N,N-dimethlyamino)pyridine / 3 h / -20 - 5 °C 1.2: 5 °C 2.1: magnesium; ethylene dibromide; N-ethyl-N,N-diisopropylamine / diethyl ether; toluene / 2 h / 100 °C 3.1: n-butyllithium / diethyl ether; hexane / 3 h / -78 °C 3.2: 20 °C 3.3: 0.08 h / 0 °C 4.1: potassium tert-butylate / tert-butyl alcohol / 1 h / Reflux 4.2: 1 h / Reflux 5.1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 0 - 5 °C 6.1: dimethylsulfide borane complex; (+)-(1R,5R)-α-pinene / tetrahydrofuran / 0 - 20 °C 6.2: 2 h / 20 °C 7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C 7.2: -78 - 0 °C 8.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.75 h / -78 - 40 °C 8.2: 0.08 h / -78 °C 9.1: formic acid / diethyl ether / 10 h / 5 - 20 °C 10.1: [bis(acetoxy)iodo]benzene; water / tetrahydrofuran / 0.67 h / 20 °C 11.1: 2,6-dimethylpyridine / dichloromethane / 4 h / 0 - 5 °C 11.2: 3 h / 5 °C 12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C 13.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 13.2: 10.33 h / 20 °C 14.1: trifluoroacetic acid / dichloromethane / 1 h / -20 - 0 °C View Scheme
参考文献
Russian Journal of Organic Chemistry, , vol. 47, # 11 p. 1653 - 1674
反应条件
1.1: magnesium; ethylene dibromide; N-ethyl-N,N-diisopropylamine / diethyl ether; toluene / 2 h / 100 °C 2.1: n-butyllithium / diethyl ether; hexane / 3 h / -78 °C 2.2: 20 °C 2.3: 0.08 h / 0 °C 3.1: potassium tert-butylate / tert-butyl alcohol / 1 h / Reflux 3.2: 1 h / Reflux 4.1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 0 - 5 °C 5.1: dimethylsulfide borane complex; (+)-(1R,5R)-α-pinene / tetrahydrofuran / 0 - 20 °C 5.2: 2 h / 20 °C 6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C 6.2: -78 - 0 °C 7.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.75 h / -78 - 40 °C 7.2: 0.08 h / -78 °C 8.1: formic acid / diethyl ether / 10 h / 5 - 20 °C 9.1: [bis(acetoxy)iodo]benzene; water / tetrahydrofuran / 0.67 h / 20 °C 10.1: 2,6-dimethylpyridine / dichloromethane / 4 h / 0 - 5 °C 10.2: 3 h / 5 °C 11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C 12.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 12.2: 10.33 h / 20 °C 13.1: trifluoroacetic acid / dichloromethane / 1 h / -20 - 0 °C View Scheme
参考文献
Russian Journal of Organic Chemistry, , vol. 47, # 11 p. 1653 - 1674
反应条件
1.1: n-butyllithium / diethyl ether; hexane / 3 h / -78 °C 1.2: 20 °C 1.3: 0.08 h / 0 °C 2.1: potassium tert-butylate / tert-butyl alcohol / 1 h / Reflux 2.2: 1 h / Reflux 3.1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 0 - 5 °C 4.1: dimethylsulfide borane complex; (+)-(1R,5R)-α-pinene / tetrahydrofuran / 0 - 20 °C 4.2: 2 h / 20 °C 5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C 5.2: -78 - 0 °C 6.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.75 h / -78 - 40 °C 6.2: 0.08 h / -78 °C 7.1: formic acid / diethyl ether / 10 h / 5 - 20 °C 8.1: [bis(acetoxy)iodo]benzene; water / tetrahydrofuran / 0.67 h / 20 °C 9.1: 2,6-dimethylpyridine / dichloromethane / 4 h / 0 - 5 °C 9.2: 3 h / 5 °C 10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C 11.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 11.2: 10.33 h / 20 °C 12.1: trifluoroacetic acid / dichloromethane / 1 h / -20 - 0 °C View Scheme
参考文献
Russian Journal of Organic Chemistry, , vol. 47, # 11 p. 1653 - 1674
反应条件
1.1: potassium tert-butylate / tert-butyl alcohol / 1 h / Reflux 1.2: 1 h / Reflux 2.1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 0 - 5 °C 3.1: dimethylsulfide borane complex; (+)-(1R,5R)-α-pinene / tetrahydrofuran / 0 - 20 °C 3.2: 2 h / 20 °C 4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C 4.2: -78 - 0 °C 5.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.75 h / -78 - 40 °C 5.2: 0.08 h / -78 °C 6.1: formic acid / diethyl ether / 10 h / 5 - 20 °C 7.1: [bis(acetoxy)iodo]benzene; water / tetrahydrofuran / 0.67 h / 20 °C 8.1: 2,6-dimethylpyridine / dichloromethane / 4 h / 0 - 5 °C 8.2: 3 h / 5 °C 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C 10.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 10.2: 10.33 h / 20 °C 11.1: trifluoroacetic acid / dichloromethane / 1 h / -20 - 0 °C View Scheme
参考文献
Russian Journal of Organic Chemistry, , vol. 47, # 11 p. 1653 - 1674
反应条件
1.1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 0 - 5 °C 2.1: dimethylsulfide borane complex; (+)-(1R,5R)-α-pinene / tetrahydrofuran / 0 - 20 °C 2.2: 2 h / 20 °C 3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C 3.2: -78 - 0 °C 4.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.75 h / -78 - 40 °C 4.2: 0.08 h / -78 °C 5.1: formic acid / diethyl ether / 10 h / 5 - 20 °C 6.1: [bis(acetoxy)iodo]benzene; water / tetrahydrofuran / 0.67 h / 20 °C 7.1: 2,6-dimethylpyridine / dichloromethane / 4 h / 0 - 5 °C 7.2: 3 h / 5 °C 8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C 9.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 9.2: 10.33 h / 20 °C 10.1: trifluoroacetic acid / dichloromethane / 1 h / -20 - 0 °C View Scheme
参考文献
Russian Journal of Organic Chemistry, , vol. 47, # 11 p. 1653 - 1674
反应条件
1.1: dimethylsulfide borane complex; (+)-(1R,5R)-α-pinene / tetrahydrofuran / 0 - 20 °C 1.2: 2 h / 20 °C 2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -78 °C 2.2: -78 - 0 °C 3.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.75 h / -78 - 40 °C 3.2: 0.08 h / -78 °C 4.1: formic acid / diethyl ether / 10 h / 5 - 20 °C 5.1: [bis(acetoxy)iodo]benzene; water / tetrahydrofuran / 0.67 h / 20 °C 6.1: 2,6-dimethylpyridine / dichloromethane / 4 h / 0 - 5 °C 6.2: 3 h / 5 °C 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C 8.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 8.2: 10.33 h / 20 °C 9.1: trifluoroacetic acid / dichloromethane / 1 h / -20 - 0 °C View Scheme
参考文献
Russian Journal of Organic Chemistry, , vol. 47, # 11 p. 1653 - 1674
反应条件
1.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / -78 °C / |Inert atmosphere 1.2: 15 h / -12 °C / |Inert atmosphere 2.1: 2,6-dimethylpyridine / dichloromethane / 5 h / -45 - 20 °C / |Inert atmosphere 3.1: (SPY-5-31)-dichloro-(κ2(C,O)-(2-isopropyloxybenzylidene))(1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene)ruthenium / 1,2-dichloro-ethane / 4 h / 80 °C / |Inert atmosphere 4.1: trifluoroacetic acid / dichloromethane / 2 h / -20 - 0 °C / |Inert atmosphere View Scheme
参考文献
European Journal of Medicinal Chemistry, , vol. 68, p. 321 - 332