Epothilone D合成路线 （共 263 条）
反应条件
1.1: 98 percent / DMAP; Et3N / CH2Cl2 / 0.75 h / 20 °C 2.1: LDA / diethyl ether / 1.17 h / -78 °C 2.2: CpTiCl(1,2:5,6-di-O-isopropylidene-α-L-glucofuranos-3-O-)2 / diethyl ether / 1.5 h / -78 - -30 °C 2.3: 85 percent / diethyl ether; H2O / 3.5 h / -78 - 20 °C 3.1: 57 percent / Cl2Ru(PCy3)(=CHPh)(N,N'-Mes2-imidazolidin-2-yl) / toluene / 25 h / 110 °C 4.1: 86 percent / nanosize Zn; AcOH / tetrahydrofuran / 0.17 h 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: 92 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C 2.1: 98 percent / DMAP; Et3N / CH2Cl2 / 0.75 h / 20 °C 3.1: LDA / diethyl ether / 1.17 h / -78 °C 3.2: CpTiCl(1,2:5,6-di-O-isopropylidene-α-L-glucofuranos-3-O-)2 / diethyl ether / 1.5 h / -78 - -30 °C 3.3: 85 percent / diethyl ether; H2O / 3.5 h / -78 - 20 °C 4.1: 57 percent / Cl2Ru(PCy3)(=CHPh)(N,N'-Mes2-imidazolidin-2-yl) / toluene / 25 h / 110 °C 5.1: 86 percent / nanosize Zn; AcOH / tetrahydrofuran / 0.17 h 6.1: 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: 100 percent / HF-pyridine / tetrahydrofuran / 12 h / 20 °C 2.1: 96 percent / Et3N; DMAP / CH2Cl2 / 6 h / 20 °C 3.1: 9-BBN / tetrahydrofuran / 1.5 h / 28 °C / microwave irradiation 3.2: 37 percent / K3PO4*3H2O; H2O / PdCl2(dppf) / tetrahydrofuran; dimethylformamide / 1 h / 60 °C 4.1: 93 percent / aq. NaOH / methanol / 36 h / 50 °C 5.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.33 h / 20 °C 5.2: 90 percent / DMAP / toluene; tetrahydrofuran / 1 h 6.1: 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: 9-BBN / tetrahydrofuran / 1.5 h / 28 °C / microwave irradiation 1.2: 37 percent / K3PO4*3H2O; H2O / PdCl2(dppf) / tetrahydrofuran; dimethylformamide / 1 h / 60 °C 2.1: 93 percent / aq. NaOH / methanol / 36 h / 50 °C 3.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.33 h / 20 °C 3.2: 90 percent / DMAP / toluene; tetrahydrofuran / 1 h 4.1: 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: LDA 2.1: 88 percent / CSA / methanol 3.1: PCC 3.2: 90 percent / NaClO2 4.1: 73 percent / TBAF 5.1: 77 percent / TCBCl; DIEA; DMAP 6.1: 59 percent / HF*pyr View Scheme
参考文献
Organic Letters, , vol. 3, # 14 p. 2221 - 2223
193146-53-1(3S,6R,7S,8S,12Z,15S,16E)-3,7,15-三-{[叔-丁基(二甲基)硅烷基]氧基}-1-羟基-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)十七-12,16-二烯-5-酮
→
反应条件
1.1: PCC 1.2: 90 percent / NaClO2 2.1: 73 percent / TBAF 3.1: 77 percent / TCBCl; DIEA; DMAP 4.1: 59 percent / HF*pyr View Scheme
参考文献
Organic Letters, , vol. 3, # 14 p. 2221 - 2223
193146-51-9(3S,6R,7S,8S,12Z,15S,16E)-1,3,7,15-四-{[叔-丁基(二甲基)硅烷基]氧基}-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)十七-12,16-二烯-5-酮
→
反应条件
1.1: 88 percent / CSA / methanol 2.1: PCC 2.2: 90 percent / NaClO2 3.1: 73 percent / TBAF 4.1: 77 percent / TCBCl; DIEA; DMAP 5.1: 59 percent / HF*pyr View Scheme
参考文献
Organic Letters, , vol. 3, # 14 p. 2221 - 2223
193146-49-5(3S,6R,7S,8S,12Z,15S,16E)-1,3,15-三-{[叔-丁基(二甲基)硅烷基]氧基}-7-羟基-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)十七烷基-12,16-二烯-5-酮
→
反应条件
1.1: 88 percent / CSA / methanol 2.1: PCC 2.2: 90 percent / NaClO2 3.1: 73 percent / TBAF 4.1: 77 percent / TCBCl; DIEA; DMAP 5.1: 59 percent / HF*pyr View Scheme
参考文献
Organic Letters, , vol. 3, # 14 p. 2221 - 2223
反应条件
1: 35 percent / LDA / tetrahydrofuran / 0.67 h / -78 °C 2: Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 3: 0.230 g / sodium borohydride / methanol; tetrahydrofuran / 1 h / -78 - 20 °C 4: 93 percent / hydrogen fluoride-pyridine; pyridine / tetrahydrofuran / 2 h / 20 °C 5: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / -30 °C 6: 94 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / 25 °C 7: 86 percent / [Mo(CHMe2Ph)(N-(2,6-(i-Pr)2C6H3))(OCMe(CF3)2)2] / benzene / 2 h / 55 °C 8: 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: [bis(trifluoroacetoxy)iodobenzene] / methanol; tetrahydrofuran / 0.25 h / 20 °C 1.2: 95 percent / pTSA*H2O / dioxane; H2O / 2 h / 50 °C 2.1: 35 percent / LDA / tetrahydrofuran / 0.67 h / -78 °C 3.1: Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 4.1: 0.230 g / sodium borohydride / methanol; tetrahydrofuran / 1 h / -78 - 20 °C 5.1: 93 percent / hydrogen fluoride-pyridine; pyridine / tetrahydrofuran / 2 h / 20 °C 6.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / -30 °C 7.1: 94 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / 25 °C 8.1: 86 percent / [Mo(CHMe2Ph)(N-(2,6-(i-Pr)2C6H3))(OCMe(CF3)2)2] / benzene / 2 h / 55 °C 9.1: 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
