Epothilone D合成路线 （共 263 条）
反应条件
1.1: thiocarbonyl diimidazole; 4-DMAP / tetrahydrofuran / 2 h / 90 °C 1.2: 0.823 g / n-Bu3SnH; AIBN / benzene / 1 h / 80 °C 2.1: [bis(trifluoroacetoxy)iodobenzene] / methanol; tetrahydrofuran / 0.25 h / 20 °C 2.2: 95 percent / pTSA*H2O / dioxane; H2O / 2 h / 50 °C 3.1: 35 percent / LDA / tetrahydrofuran / 0.67 h / -78 °C 4.1: Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 5.1: 0.230 g / sodium borohydride / methanol; tetrahydrofuran / 1 h / -78 - 20 °C 6.1: 93 percent / hydrogen fluoride-pyridine; pyridine / tetrahydrofuran / 2 h / 20 °C 7.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / -30 °C 8.1: 94 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / 25 °C 9.1: 86 percent / [Mo(CHMe2Ph)(N-(2,6-(i-Pr)2C6H3))(OCMe(CF3)2)2] / benzene / 2 h / 55 °C 10.1: 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
n-butyllithium; tungsten hexachloride in tetrahydrofuran deoxygenation;
参考文献
Johnson; Kim; Bifano; DiMarco; Fairchild; Gougoutas; Lee; Long; Tokarski; Vite
Organic letters, 2000 , vol. 2, # 11 p. 1537 - 1540
反应条件
1: LDA / tetrahydrofuran / 0.58 h / -90 °C 2: 97 percent / 2,6-lutidine / CH2Cl2 / -40 - -20 °C 3: 98 percent / p-TsOH*H2O; H2O / tetrahydrofuran / 6.5 h / 64 °C 4: 86 percent / LDA; CpTiCl(O-1,2:5,6-di-O-isopropylidene-L-glucofurans-3-O-yl)2 / diethyl ether / 2 h / -78 °C 5: 98 percent / imidazole / dimethylformamide / 2 h / 20 °C 6: 83 percent / H2 / 10percent Pd/C / ethanol / 0.5 h 7: 95 percent / TPAP; NMO / CH2Cl2 / 0.8 h / 20 °C 8: 78 percent / n-BuLi / tetrahydrofuran; hexane / -78 - -5 °C 9: TESOTf; 2,6-lutidine / CH2Cl2 / 3 h / 20 °C 10: 380 mg / EDCI; DMAP / CH2Cl2 / 2 h / 20 °C 11: 78 percent / Cl2(PCy3)Ru(=CHPh)[cyclo(CHNMesCH2CH2NMes)] / toluene / 0.17 h / 110 °C 12: 76 percent / KHMDS / tetrahydrofuran; toluene / -78 - -20 °C 13: 97 percent / HF*pyridine / tetrahydrofuran / 3 h / 20 °C 14: 91 percent / TrisNHNH2; Et3N / 1,2-dichloro-ethane / 7 h / 50 °C View Scheme
参考文献
Journal of the American Chemical Society, , vol. 125, # 10 p. 2899 - 2901
反应条件
1: 86 percent / LDA; CpTiCl(O-1,2:5,6-di-O-isopropylidene-L-glucofurans-3-O-yl)2 / diethyl ether / 2 h / -78 °C 2: 98 percent / imidazole / dimethylformamide / 2 h / 20 °C 3: 83 percent / H2 / 10percent Pd/C / ethanol / 0.5 h 4: 95 percent / TPAP; NMO / CH2Cl2 / 0.8 h / 20 °C 5: 78 percent / n-BuLi / tetrahydrofuran; hexane / -78 - -5 °C 6: TESOTf; 2,6-lutidine / CH2Cl2 / 3 h / 20 °C 7: 380 mg / EDCI; DMAP / CH2Cl2 / 2 h / 20 °C 8: 78 percent / Cl2(PCy3)Ru(=CHPh)[cyclo(CHNMesCH2CH2NMes)] / toluene / 0.17 h / 110 °C 9: 76 percent / KHMDS / tetrahydrofuran; toluene / -78 - -20 °C 10: 97 percent / HF*pyridine / tetrahydrofuran / 3 h / 20 °C 11: 91 percent / TrisNHNH2; Et3N / 1,2-dichloro-ethane / 7 h / 50 °C View Scheme
参考文献
Journal of the American Chemical Society, , vol. 125, # 10 p. 2899 - 2901
反应条件
1: 98 percent / p-TsOH*H2O; H2O / tetrahydrofuran / 6.5 h / 64 °C 2: 86 percent / LDA; CpTiCl(O-1,2:5,6-di-O-isopropylidene-L-glucofurans-3-O-yl)2 / diethyl ether / 2 h / -78 °C 3: 98 percent / imidazole / dimethylformamide / 2 h / 20 °C 4: 83 percent / H2 / 10percent Pd/C / ethanol / 0.5 h 5: 95 percent / TPAP; NMO / CH2Cl2 / 0.8 h / 20 °C 6: 78 percent / n-BuLi / tetrahydrofuran; hexane / -78 - -5 °C 7: TESOTf; 2,6-lutidine / CH2Cl2 / 3 h / 20 °C 8: 380 mg / EDCI; DMAP / CH2Cl2 / 2 h / 20 °C 9: 78 percent / Cl2(PCy3)Ru(=CHPh)[cyclo(CHNMesCH2CH2NMes)] / toluene / 0.17 h / 110 °C 10: 76 percent / KHMDS / tetrahydrofuran; toluene / -78 - -20 °C 11: 97 percent / HF*pyridine / tetrahydrofuran / 3 h / 20 °C 12: 91 percent / TrisNHNH2; Et3N / 1,2-dichloro-ethane / 7 h / 50 °C View Scheme
参考文献
Journal of the American Chemical Society, , vol. 125, # 10 p. 2899 - 2901
反应条件
1: 98 percent / imidazole / dimethylformamide / 2 h / 20 °C 2: 83 percent / H2 / 10percent Pd/C / ethanol / 0.5 h 3: 95 percent / TPAP; NMO / CH2Cl2 / 0.8 h / 20 °C 4: 78 percent / n-BuLi / tetrahydrofuran; hexane / -78 - -5 °C 5: TESOTf; 2,6-lutidine / CH2Cl2 / 3 h / 20 °C 6: 380 mg / EDCI; DMAP / CH2Cl2 / 2 h / 20 °C 7: 78 percent / Cl2(PCy3)Ru(=CHPh)[cyclo(CHNMesCH2CH2NMes)] / toluene / 0.17 h / 110 °C 8: 76 percent / KHMDS / tetrahydrofuran; toluene / -78 - -20 °C 9: 97 percent / HF*pyridine / tetrahydrofuran / 3 h / 20 °C 10: 91 percent / TrisNHNH2; Et3N / 1,2-dichloro-ethane / 7 h / 50 °C View Scheme
参考文献
Journal of the American Chemical Society, , vol. 125, # 10 p. 2899 - 2901
反应条件
1: 83 percent / H2 / 10percent Pd/C / ethanol / 0.5 h 2: 95 percent / TPAP; NMO / CH2Cl2 / 0.8 h / 20 °C 3: 78 percent / n-BuLi / tetrahydrofuran; hexane / -78 - -5 °C 4: TESOTf; 2,6-lutidine / CH2Cl2 / 3 h / 20 °C 5: 380 mg / EDCI; DMAP / CH2Cl2 / 2 h / 20 °C 6: 78 percent / Cl2(PCy3)Ru(=CHPh)[cyclo(CHNMesCH2CH2NMes)] / toluene / 0.17 h / 110 °C 7: 76 percent / KHMDS / tetrahydrofuran; toluene / -78 - -20 °C 8: 97 percent / HF*pyridine / tetrahydrofuran / 3 h / 20 °C 9: 91 percent / TrisNHNH2; Et3N / 1,2-dichloro-ethane / 7 h / 50 °C View Scheme
参考文献
Journal of the American Chemical Society, , vol. 125, # 10 p. 2899 - 2901
反应条件
1.1: 92 percent / 2,6-lutidine / CH2Cl2 / 15 h / 0 - 20 °C 2.1: 76 percent / EDCI; DMAP / CH2Cl2 / 2 h / 0 - 20 °C 3.1: Cl2Ru(PCy3)=(CHPh)(N,N'-Mes2-imidazolidin-2-yl) / CH2Cl2 / 5 h / 35 °C 3.2: 56 percent / nanosize Zn; AcOH / tetrahydrofuran / 0.17 h 4.1: 90 percent / HF*Py / tetrahydrofuran / 3 h / 20 °C 5.1: 86 percent / potassium diazodicarboxylate; AcOH / CH2Cl2 / Heating View Scheme
参考文献
Journal of the American Chemical Society, , vol. 124, # 33 p. 9825 - 9832
反应条件
1.1: LDA / diethyl ether / 1.17 h / -78 °C 1.2: CpTiCl(1,2:5,6-di-O-isopropylidene-α-L-glucofuranos-3-O-)2 / diethyl ether / 1.5 h / -78 - -30 °C 1.3: 85 percent / diethyl ether; H2O / 3.5 h / -78 - 20 °C 2.1: 57 percent / Cl2Ru(PCy3)(=CHPh)(N,N'-Mes2-imidazolidin-2-yl) / toluene / 25 h / 110 °C 3.1: 86 percent / nanosize Zn; AcOH / tetrahydrofuran / 0.17 h 4.1: 86 percent / potassium diazodicarboxylate; AcOH / CH2Cl2 / Heating View Scheme
参考文献
Journal of the American Chemical Society, , vol. 124, # 33 p. 9825 - 9832
反应条件
1.1: 76 percent / EDCI; DMAP / CH2Cl2 / 2 h / 0 - 20 °C 2.1: Cl2Ru(PCy3)=(CHPh)(N,N'-Mes2-imidazolidin-2-yl) / CH2Cl2 / 5 h / 35 °C 2.2: 56 percent / nanosize Zn; AcOH / tetrahydrofuran / 0.17 h 3.1: 90 percent / HF*Py / tetrahydrofuran / 3 h / 20 °C 4.1: 86 percent / potassium diazodicarboxylate; AcOH / CH2Cl2 / Heating View Scheme
参考文献
Journal of the American Chemical Society, , vol. 124, # 33 p. 9825 - 9832
