Epothilone D合成路线 （共 263 条）
反应条件
1.1: 83 percent / benzene / Heating 2.1: 60 percent / (S)-(-)-1,1'-bi-2-naphthol; Ti(O-i-Pr)4; 4 Angstroem sieves / CH2Cl2 / 70 h / -78 - -20 °C 3.1: 96 percent / 4-DMAP; Et3N / CH2Cl2 / 2 h 4.1: N-methylmorpholine N-oxide; water / OsO4 / acetone; butan-1-ol / 2 h / 0 °C 5.1: NaIO4 / tetrahydrofuran; H2O / 1.25 h / 20 °C 6.1: 0.141 g / tetrahydrofuran; hexane / 0.67 h / -20 °C 7.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 5 h / 20 °C 7.2: 77 percent / Cs2CO3; Ph3As; H2O / PdCl2(1,1'-bis(diphenylphosphino)ferrocene)2 / dimethylformamide; tetrahydrofuran / 3 h / 20 °C 8.1: 71 percent / pTSA*H2O / dioxane; H2O / 3 h / 55 °C 9.1: 0.055 g / potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C 10.1: Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 11.1: 0.052 g / NaBH4 / methanol; tetrahydrofuran / 1 h / -78 - 20 °C 12.1: 94 percent / hydrogen fluoride-pyridine; pyridine / tetrahydrofuran / 2 h / 20 °C 13.1: 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
1.1: N-methylmorpholine N-oxide; water / OsO4 / acetone; butan-1-ol / 2 h / 0 °C 2.1: NaIO4 / tetrahydrofuran; H2O / 1.25 h / 20 °C 3.1: 0.141 g / tetrahydrofuran; hexane / 0.67 h / -20 °C 4.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 5 h / 20 °C 4.2: 77 percent / Cs2CO3; Ph3As; H2O / PdCl2(1,1'-bis(diphenylphosphino)ferrocene)2 / dimethylformamide; tetrahydrofuran / 3 h / 20 °C 5.1: 71 percent / pTSA*H2O / dioxane; H2O / 3 h / 55 °C 6.1: 0.055 g / potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C 7.1: Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 8.1: 0.052 g / NaBH4 / methanol; tetrahydrofuran / 1 h / -78 - 20 °C 9.1: 94 percent / hydrogen fluoride-pyridine; pyridine / tetrahydrofuran / 2 h / 20 °C 10.1: 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
pyridine hydrogenfluoride in tetrahydrofuran T=20°C; desilylation; 1.5 h;
参考文献
Journal of the American Chemical Society, , vol. 119, # 42 p. 10073 - 10092
193146-26-8(3S,6R,7S,12Z,15S,16E)-3,7-二-{[叔-丁基(二甲基)硅烷基]氧基}-15-羟基-4,4,6,8,12,16-六甲基-17-(2-甲基-1,3-噻唑-4-基)-5-氧代十七碳-12,16-二烯酸
→
反应条件
1: 62 percent / 2,4,6-trichlorobenzoyl chloride; DMAP 2: 91 percent / CF3CO2H / CH2Cl2 View Scheme
参考文献
Tetrahedron Letters, , vol. 42, # 47 p. 8373 - 8377
反应条件
1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C 1.2: 92 percent / tetrahydrofuran; hexane / 2 h / -78 - 20 °C 2.1: 99 percent / Mg; 1,2-dibromoethane / diethyl ether / 3.5 h / 20 °C 3.1: Et3N / CH2Cl2 / 0.17 h / 0 °C 4.1: 84 percent / LiBr / acetone; CH2Cl2 / 1.8 h / 20 °C 5.1: CuI; Et3N / diethyl ether; dimethylformamide / 20 °C 5.2: 60 percent / diethyl ether; dimethylformamide / 18 h / 20 °C 6.1: 68 percent / H2; Pb(OAc)2 / Pd/CaCO3 / hexane / 28 h / 20 °C 7.1: 66 percent / aq. NaOH / propan-2-ol / 16 h / 45 °C 8.1: 89 percent / TBAF / tetrahydrofuran / 16 h / 0 - 25 °C 9.1: 1,3,5-Cl3C6H2COCl; Et3N / tetrahydrofuran / 0.75 h / 0 °C 9.2: 63 percent / DMAP / toluene; tetrahydrofuran / 4.5 h / 75 °C 10.1: 83 percent / TFA / CH2Cl2 / 4.5 h / 0 °C 11.1: 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: 82 percent / CuI / diethyl ether / 0.5 h / -50 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C 2.2: 92 percent / tetrahydrofuran; hexane / 2 h / -78 - 20 °C 3.1: 99 percent / Mg; 1,2-dibromoethane / diethyl ether / 3.5 h / 20 °C 4.1: Et3N / CH2Cl2 / 0.17 h / 0 °C 5.1: 84 percent / LiBr / acetone; CH2Cl2 / 1.8 h / 20 °C 6.1: CuI; Et3N / diethyl ether; dimethylformamide / 20 °C 6.2: 60 percent / diethyl ether; dimethylformamide / 18 h / 20 °C 7.1: 68 percent / H2; Pb(OAc)2 / Pd/CaCO3 / hexane / 28 h / 20 °C 8.1: 66 percent / aq. NaOH / propan-2-ol / 16 h / 45 °C 9.1: 89 percent / TBAF / tetrahydrofuran / 16 h / 0 - 25 °C 10.1: 1,3,5-Cl3C6H2COCl; Et3N / tetrahydrofuran / 0.75 h / 0 °C 10.2: 63 percent / DMAP / toluene; tetrahydrofuran / 4.5 h / 75 °C 11.1: 83 percent / TFA / CH2Cl2 / 4.5 h / 0 °C 12.1: 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: NaHMDS / tetrahydrofuran / 0.83 h / -78 °C 1.2: Davis' oxaziridine / tetrahydrofuran / 0.1 h 1.3: 71 percent / CSA / tetrahydrofuran / 0.03 h 2.1: 90 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / -78 °C 3.1: 90 percent / KSEt; KH / tetrahydrofuran / 0 - 20 °C 4.1: 82 percent / CuI / diethyl ether / 0.5 h / -50 °C 5.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C 5.2: 92 percent / tetrahydrofuran; hexane / 2 h / -78 - 20 °C 6.1: 99 percent / Mg; 1,2-dibromoethane / diethyl ether / 3.5 h / 20 °C 7.1: Et3N / CH2Cl2 / 0.17 h / 0 °C 8.1: 84 percent / LiBr / acetone; CH2Cl2 / 1.8 h / 20 °C 9.1: CuI; Et3N / diethyl ether; dimethylformamide / 20 °C 9.2: 60 percent / diethyl ether; dimethylformamide / 18 h / 20 °C 10.1: 68 percent / H2; Pb(OAc)2 / Pd/CaCO3 / hexane / 28 h / 20 °C 11.1: 66 percent / aq. NaOH / propan-2-ol / 16 h / 45 °C 12.1: 89 percent / TBAF / tetrahydrofuran / 16 h / 0 - 25 °C 13.1: 1,3,5-Cl3C6H2COCl; Et3N / tetrahydrofuran / 0.75 h / 0 °C 13.2: 63 percent / DMAP / toluene; tetrahydrofuran / 4.5 h / 75 °C 14.1: 83 percent / TFA / CH2Cl2 / 4.5 h / 0 °C 15.1: 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: hexamethyldisilazane; n-BuLi / tetrahydrofuran; hexane / -78 - -30 °C 1.2: 82 percent / tetrahydrofuran; hexane / 70 h / -78 - 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: 99 percent / Mg; 1,2-dibromoethane / diethyl ether / 3.5 h / 20 °C 2.1: Et3N / CH2Cl2 / 0.17 h / 0 °C 3.1: 84 percent / LiBr / acetone; CH2Cl2 / 1.8 h / 20 °C 4.1: CuI; Et3N / diethyl ether; dimethylformamide / 20 °C 4.2: 60 percent / diethyl ether; dimethylformamide / 18 h / 20 °C 5.1: 68 percent / H2; Pb(OAc)2 / Pd/CaCO3 / hexane / 28 h / 20 °C 6.1: 66 percent / aq. NaOH / propan-2-ol / 16 h / 45 °C 7.1: 89 percent / TBAF / tetrahydrofuran / 16 h / 0 - 25 °C 8.1: 1,3,5-Cl3C6H2COCl; Et3N / tetrahydrofuran / 0.75 h / 0 °C 8.2: 63 percent / DMAP / toluene; tetrahydrofuran / 4.5 h / 75 °C 9.1: 83 percent / TFA / CH2Cl2 / 4.5 h / 0 °C 10.1: 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: 90 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / -78 °C 2.1: 90 percent / KSEt; KH / tetrahydrofuran / 0 - 20 °C 3.1: 82 percent / CuI / diethyl ether / 0.5 h / -50 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C 4.2: 92 percent / tetrahydrofuran; hexane / 2 h / -78 - 20 °C 5.1: 99 percent / Mg; 1,2-dibromoethane / diethyl ether / 3.5 h / 20 °C 6.1: Et3N / CH2Cl2 / 0.17 h / 0 °C 7.1: 84 percent / LiBr / acetone; CH2Cl2 / 1.8 h / 20 °C 8.1: CuI; Et3N / diethyl ether; dimethylformamide / 20 °C 8.2: 60 percent / diethyl ether; dimethylformamide / 18 h / 20 °C 9.1: 68 percent / H2; Pb(OAc)2 / Pd/CaCO3 / hexane / 28 h / 20 °C 10.1: 66 percent / aq. NaOH / propan-2-ol / 16 h / 45 °C 11.1: 89 percent / TBAF / tetrahydrofuran / 16 h / 0 - 25 °C 12.1: 1,3,5-Cl3C6H2COCl; Et3N / tetrahydrofuran / 0.75 h / 0 °C 12.2: 63 percent / DMAP / toluene; tetrahydrofuran / 4.5 h / 75 °C 13.1: 83 percent / TFA / CH2Cl2 / 4.5 h / 0 °C 14.1: 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
