Epothilone D合成路线 （共 263 条）
反应条件
1.1: NMO; OsO4 / 2-methyl-propan-2-ol; H2O 2.1: H5IO6 3.1: tetrahydrofuran / 0.5 h / -78 °C 4.1: iPr2NEt / CH2Cl2 / -78 °C 5.1: PPTS / ethanol / 20 °C 6.1: 96 percent / NMO; TPAP; mol sieves 4 Angstroem / acetonitrile 7.1: LiHMDS / tetrahydrofuran / -78 °C 7.2: 80 percent / tetrahydrofuran 8.1: TMSOTf; collidine / CH2Cl2 / 1 h / 0 °C 8.2: 85 percent / nBu4NF / tetrahydrofuran 9.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 1 h / 20 °C 9.2: 60 percent / DMAP / toluene / 80 °C 10.1: 86 percent / TFA / CH2Cl2 / 0 °C 11.1: 71 percent / 2,4,6-triisopropylbenzenesulfonyl hydrazide; Et3N / diethyl ether / 39 °C View Scheme
参考文献
Tetrahedron Letters, , vol. 43, # 16 p. 2895 - 2898
反应条件
1.1: LiHMDS / tetrahydrofuran / -78 °C 1.2: 80 percent / tetrahydrofuran 2.1: TMSOTf; collidine / CH2Cl2 / 1 h / 0 °C 2.2: 85 percent / nBu4NF / tetrahydrofuran 3.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 1 h / 20 °C 3.2: 60 percent / DMAP / toluene / 80 °C 4.1: 86 percent / TFA / CH2Cl2 / 0 °C 5.1: 71 percent / 2,4,6-triisopropylbenzenesulfonyl hydrazide; Et3N / diethyl ether / 39 °C View Scheme
参考文献
Tetrahedron Letters, , vol. 43, # 16 p. 2895 - 2898
反应条件
1.1: 96 percent / NMO; TPAP; mol sieves 4 Angstroem / acetonitrile 2.1: LiHMDS / tetrahydrofuran / -78 °C 2.2: 80 percent / tetrahydrofuran 3.1: TMSOTf; collidine / CH2Cl2 / 1 h / 0 °C 3.2: 85 percent / nBu4NF / tetrahydrofuran 4.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 1 h / 20 °C 4.2: 60 percent / DMAP / toluene / 80 °C 5.1: 86 percent / TFA / CH2Cl2 / 0 °C 6.1: 71 percent / 2,4,6-triisopropylbenzenesulfonyl hydrazide; Et3N / diethyl ether / 39 °C View Scheme
参考文献
Tetrahedron Letters, , vol. 43, # 16 p. 2895 - 2898
反应条件
1.1: TMSOTf; collidine / CH2Cl2 / 1 h / 0 °C 1.2: 85 percent / nBu4NF / tetrahydrofuran 2.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 1 h / 20 °C 2.2: 60 percent / DMAP / toluene / 80 °C 3.1: 86 percent / TFA / CH2Cl2 / 0 °C 4.1: 71 percent / 2,4,6-triisopropylbenzenesulfonyl hydrazide; Et3N / diethyl ether / 39 °C View Scheme
参考文献
Tetrahedron Letters, , vol. 43, # 16 p. 2895 - 2898
反应条件
1.1: Amberlyst 15 2.1: imid. 3.1: 78 percent / i-Pr2EtN 4.1: Bu3SnH; AIBN 4.2: SnBr4 / -78 °C 5.1: 80 percent / pyridine 6.1: 59 percent / Bu3SnH; AIBN 7.1: 91 percent / DDQ 8.1: 97 percent / Bu4NF 9.1: Dess-Martin periodinane 10.1: 99 percent / Dess-Martin periodinane 11.1: 74 percent / n-BuLi 12.1: DIBAL-H 13.1: Dess-Martin periodinane 14.1: 67 percent / Li(i-Pr)2N / -78 °C 15.1: 79 percent / Cl2CHCO2H 16.1: Dess-Martin periodinane 17.1: NaClO2 18.1: MgBr2; n-BuSH; K2CO3 19.1: 62 percent / 2,4,6-trichlorobenzoyl chloride; DMAP 20.1: 91 percent / CF3CO2H / CH2Cl2 View Scheme
参考文献
Tetrahedron Letters, , vol. 42, # 47 p. 8373 - 8377
反应条件
1: 67 percent / Dess-Martin periodinane / CH2Cl2 / Ambient temperature 2: 80 percent / HF*pyridine / tetrahydrofuran / Ambient temperature View Scheme
参考文献
Angewandte Chemie (International Edition in English), , vol. 36, # 7 p. 757 - 759
反应条件
1.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.75 h / -78 - 40 °C 1.2: 0.08 h / -78 °C 2.1: formic acid / diethyl ether / 10 h / 5 - 20 °C 3.1: [bis(acetoxy)iodo]benzene; water / tetrahydrofuran / 0.67 h / 20 °C 4.1: 2,6-dimethylpyridine / dichloromethane / 4 h / 0 - 5 °C 4.2: 3 h / 5 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C 6.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 6.2: 10.33 h / 20 °C 7.1: 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: pyridinium p-toluenesulfonate; dimethyl sulfoxide / 4 h / 65 °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: formic acid / diethyl ether / 10 h / 5 - 20 °C 2.1: [bis(acetoxy)iodo]benzene; water / tetrahydrofuran / 0.67 h / 20 °C 3.1: 2,6-dimethylpyridine / dichloromethane / 4 h / 0 - 5 °C 3.2: 3 h / 5 °C 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C 5.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 5.2: 10.33 h / 20 °C 6.1: 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: [bis(acetoxy)iodo]benzene; water / tetrahydrofuran / 0.67 h / 20 °C 2.1: 2,6-dimethylpyridine / dichloromethane / 4 h / 0 - 5 °C 2.2: 3 h / 5 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C 4.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 4.2: 10.33 h / 20 °C 5.1: 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
