Epothilone D合成路线 （共 263 条）
反应条件
1: 57 percent / Cl2Ru(PCy3)(=CHPh)(N,N'-Mes2-imidazolidin-2-yl) / toluene / 25 h / 110 °C 2: 86 percent / nanosize Zn; AcOH / tetrahydrofuran / 0.17 h 3: 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: Cl2Ru(PCy3)=(CHPh)(N,N'-Mes2-imidazolidin-2-yl) / CH2Cl2 / 5 h / 35 °C 1.2: 56 percent / nanosize Zn; AcOH / tetrahydrofuran / 0.17 h 2.1: 90 percent / HF*Py / tetrahydrofuran / 3 h / 20 °C 3.1: 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: 68 percent / H2; Pb(OAc)2 / Pd/CaCO3 / hexane / 28 h / 20 °C 2.1: 66 percent / aq. NaOH / propan-2-ol / 16 h / 45 °C 3.1: 89 percent / TBAF / tetrahydrofuran / 16 h / 0 - 25 °C 4.1: 1,3,5-Cl3C6H2COCl; Et3N / tetrahydrofuran / 0.75 h / 0 °C 4.2: 63 percent / DMAP / toluene; tetrahydrofuran / 4.5 h / 75 °C 5.1: 83 percent / TFA / CH2Cl2 / 4.5 h / 0 °C 6.1: 52 percent / KO2CN=NCO2K; AcOH / CH2Cl2 / 25 h / Heating View Scheme
参考文献
Journal of the American Chemical Society, , vol. 123, # 23 p. 5407 - 5413
反应条件
1.1: K2CO3; SnCl4; bis(trimethylsilyl)peroxide / trans-1,2-bisNHTs-cyclohexane; MS 4A / CH2Cl2 / 10 h / 0 °C 2.1: BCl3 / CH2Cl2; xylene / 0.33 h / -78 °C 3.1: diisopropylethylamine / CH2Cl2 / 0.5 h 4.1: Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C 5.1: 9-BBN / tetrahydrofuran / 1.5 h / 28 °C / microwave irradiation 5.2: 37 percent / K3PO4*3H2O; H2O / PdCl2(dppf) / tetrahydrofuran; dimethylformamide / 1 h / 60 °C 6.1: 93 percent / aq. NaOH / methanol / 36 h / 50 °C 7.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.33 h / 20 °C 7.2: 90 percent / DMAP / toluene; tetrahydrofuran / 1 h 8.1: 92 percent / HF*pyridine / tetrahydrofuran View Scheme
参考文献
Journal of the American Chemical Society, , vol. 122, # 43 p. 10521 - 10532
反应条件
1.1: CuI; Et3N / diethyl ether; dimethylformamide / 20 °C 1.2: 60 percent / diethyl ether; dimethylformamide / 18 h / 20 °C 2.1: 68 percent / H2; Pb(OAc)2 / Pd/CaCO3 / hexane / 28 h / 20 °C 3.1: 66 percent / aq. NaOH / propan-2-ol / 16 h / 45 °C 4.1: 89 percent / TBAF / tetrahydrofuran / 16 h / 0 - 25 °C 5.1: 1,3,5-Cl3C6H2COCl; Et3N / tetrahydrofuran / 0.75 h / 0 °C 5.2: 63 percent / DMAP / toluene; tetrahydrofuran / 4.5 h / 75 °C 6.1: 83 percent / TFA / CH2Cl2 / 4.5 h / 0 °C 7.1: 52 percent / KO2CN=NCO2K; AcOH / CH2Cl2 / 25 h / Heating View Scheme
参考文献
Journal of the American Chemical Society, , vol. 123, # 23 p. 5407 - 5413
反应条件
1: LDA / tetrahydrofuran / 1.) -33 deg C, 5 min, 2.) -120 deg C 2: pyridine / CH2Cl2 / 0 - 25 °C 3: HCl / methanol / 0 °C 4: 1.) 9-BBN, 2.) Ph3As, Cs2CO3, H2O / 2.) <Pd(dppf)Cl2> / 1.) THF, 2.) DMF 5: HCl / methanol 6: 88 percent / H2, HCl / <(R)-(binap)RuCl2> / methanol / 7 h / 25 °C / 62255 Torr 7: 2,6-lutidine / CH2Cl2 / -78 - 25 °C 8: HCl / methanol 9: 78 percent / 2,4,6-trichlorobenzoyl chloride, Et3N, 4-DMAP / toluene 10: 95 percent / SmI2 / NiI2 / tetrahydrofuran / -78 °C 11: 98 percent / HF*pyridine / tetrahydrofuran View Scheme
参考文献
Angewandte Chemie - International Edition, , vol. 37, # 19 p. 2675 - 2678
反应条件
1: 1.) 9-BBN, 2.) Ph3As, Cs2CO3, H2O / 2.) <Pd(dppf)Cl2> / 1.) THF, 2.) DMF 2: HCl / methanol 3: 88 percent / H2, HCl / <(R)-(binap)RuCl2> / methanol / 7 h / 25 °C / 62255 Torr 4: 2,6-lutidine / CH2Cl2 / -78 - 25 °C 5: HCl / methanol 6: 78 percent / 2,4,6-trichlorobenzoyl chloride, Et3N, 4-DMAP / toluene 7: 95 percent / SmI2 / NiI2 / tetrahydrofuran / -78 °C 8: 98 percent / HF*pyridine / tetrahydrofuran View Scheme
参考文献
Angewandte Chemie - International Edition, , vol. 37, # 19 p. 2675 - 2678
反应条件
1: pyridine / CH2Cl2 / 0 - 25 °C 2: HCl / methanol / 0 °C 3: 1.) 9-BBN, 2.) Ph3As, Cs2CO3, H2O / 2.) <Pd(dppf)Cl2> / 1.) THF, 2.) DMF 4: HCl / methanol 5: 88 percent / H2, HCl / <(R)-(binap)RuCl2> / methanol / 7 h / 25 °C / 62255 Torr 6: 2,6-lutidine / CH2Cl2 / -78 - 25 °C 7: HCl / methanol 8: 78 percent / 2,4,6-trichlorobenzoyl chloride, Et3N, 4-DMAP / toluene 9: 95 percent / SmI2 / NiI2 / tetrahydrofuran / -78 °C 10: 98 percent / HF*pyridine / tetrahydrofuran View Scheme
参考文献
Angewandte Chemie - International Edition, , vol. 37, # 19 p. 2675 - 2678
反应条件
1: HCl / methanol 2: 78 percent / 2,4,6-trichlorobenzoyl chloride, Et3N, 4-DMAP / toluene 3: 95 percent / SmI2 / NiI2 / tetrahydrofuran / -78 °C 4: 98 percent / HF*pyridine / tetrahydrofuran View Scheme
参考文献
Angewandte Chemie - International Edition, , vol. 37, # 19 p. 2675 - 2678
反应条件
1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / -30 °C 2: 94 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / 25 °C 3: 86 percent / [Mo(CHMe2Ph)(N-(2,6-(i-Pr)2C6H3))(OCMe(CF3)2)2] / benzene / 2 h / 55 °C 4: 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
