Epothilone D合成路线 （共 263 条）
反应条件
1: Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 2: 0.230 g / sodium borohydride / methanol; tetrahydrofuran / 1 h / -78 - 20 °C 3: 93 percent / hydrogen fluoride-pyridine; pyridine / tetrahydrofuran / 2 h / 20 °C 4: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / -30 °C 5: 94 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / 25 °C 6: 86 percent / [Mo(CHMe2Ph)(N-(2,6-(i-Pr)2C6H3))(OCMe(CF3)2)2] / benzene / 2 h / 55 °C 7: HF*pyridine / tetrahydrofuran / 1.5 h / 20 °C View Scheme
参考文献
Journal of the American Chemical Society, , vol. 119, # 42 p. 10073 - 10092
反应条件
1: 93 percent / hydrogen fluoride-pyridine; pyridine / tetrahydrofuran / 2 h / 20 °C 2: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / -30 °C 3: 94 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / 25 °C 4: 86 percent / [Mo(CHMe2Ph)(N-(2,6-(i-Pr)2C6H3))(OCMe(CF3)2)2] / benzene / 2 h / 55 °C 5: HF*pyridine / tetrahydrofuran / 1.5 h / 20 °C View Scheme
参考文献
Journal of the American Chemical Society, , vol. 119, # 42 p. 10073 - 10092
反应条件
1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C 1.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C 2.1: pyridine / CH2Cl2 / 1 h / 0 °C 3.1: CH2Cl2 / 5 h / 20 °C 4.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C 5.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 6.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 6.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 7.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 8.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 69, # 26 p. 9269 - 9284
反应条件
1: 86 percent / TFA / CH2Cl2 / 0 °C 2: 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: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran / 1 h / 20 °C 1.2: 60 percent / DMAP / toluene / 80 °C 2.1: 86 percent / TFA / CH2Cl2 / 0 °C 3.1: 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: OsO4 1.2: 80 percent / NaIO4 2.1: 93 percent / NiCl2; CrCl2 / dimethylformamide / 0.67 h / 20 °C 3.1: 87 percent / SOCl2 / diethyl ether; pentane / 6.5 h / -78 - 0 °C 4.1: 88 percent / LiEt3BH / tetrahydrofuran / 2 h / -78 - 20 °C 5.1: 80 percent / PCC 6.1: LDA 7.1: 88 percent / CSA / methanol 8.1: PCC 8.2: 90 percent / NaClO2 9.1: 73 percent / TBAF 10.1: 77 percent / TCBCl; DIEA; DMAP 11.1: 59 percent / HF*pyr View Scheme
参考文献
Organic Letters, , vol. 3, # 14 p. 2221 - 2223
反应条件
1: 380 mg / NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; various solvent(s); H2O / 3 h 2: 55 percent / TBAF / tetrahydrofuran / 10 h / 20 °C 3: 69 percent / N-ethyl-N'-(3-(dimethylamino)propyl)carbodiimide *HCl; DMAP; DMAP*HCl / CHCl3 / 17 h / Heating 4: 96 percent / HF*Py; Py / tetrahydrofuran / 36 h / 0 - 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 65, # 22 p. 7456 - 7467
反应条件
1.1: 0.141 g / tetrahydrofuran; hexane / 0.67 h / -20 °C 2.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 5 h / 20 °C 2.2: 77 percent / Cs2CO3; Ph3As; H2O / PdCl2(1,1'-bis(diphenylphosphino)ferrocene)2 / dimethylformamide; tetrahydrofuran / 3 h / 20 °C 3.1: 71 percent / pTSA*H2O / dioxane; H2O / 3 h / 55 °C 4.1: 0.055 g / potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C 5.1: Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 6.1: 0.052 g / NaBH4 / methanol; tetrahydrofuran / 1 h / -78 - 20 °C 7.1: 94 percent / hydrogen fluoride-pyridine; pyridine / tetrahydrofuran / 2 h / 20 °C 8.1: 92 percent / HF*pyridine / tetrahydrofuran / 2 h / 0 - 20 °C View Scheme
参考文献
Journal of the American Chemical Society, , vol. 119, # 42 p. 10073 - 10092
反应条件
1: 0.055 g / potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C 2: Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 3: 0.052 g / NaBH4 / methanol; tetrahydrofuran / 1 h / -78 - 20 °C 4: 94 percent / hydrogen fluoride-pyridine; pyridine / tetrahydrofuran / 2 h / 20 °C 5: 92 percent / HF*pyridine / tetrahydrofuran / 2 h / 0 - 20 °C View Scheme
参考文献
Journal of the American Chemical Society, , vol. 119, # 42 p. 10073 - 10092
反应条件
1: 71 percent / pTSA*H2O / dioxane; H2O / 3 h / 55 °C 2: 0.055 g / potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C 3: Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 4: 0.052 g / NaBH4 / methanol; tetrahydrofuran / 1 h / -78 - 20 °C 5: 94 percent / hydrogen fluoride-pyridine; pyridine / tetrahydrofuran / 2 h / 20 °C 6: 92 percent / HF*pyridine / tetrahydrofuran / 2 h / 0 - 20 °C View Scheme
参考文献
Journal of the American Chemical Society, , vol. 119, # 42 p. 10073 - 10092
