(5S)-3-[(2S,13R)-2,13-二羟基-13-[(2R,5R)-5-[(2R,5R)-5-[(1R)-1-羟基十一烷基]四氢呋喃-2-基]四氢呋喃-2-基]十三烷基]-5-甲基-5H-呋喃-2-酮合成路线 （共 102 条）
反应条件
1: H2 / Rh(PPh3)3Cl / ethanol; benzene / 2 h / Ambient temperature 2: BF3*Et2O, Me2S / CH2Cl2 / 0.5 h / 0 deg C -> r.t. View Scheme
参考文献
Tetrahedron Letters, , vol. 36, # 51 p. 9257 - 9260
反应条件
1: 74 percent / InBr3 / ethyl acetate / 18 h / 20 °C 2: 89 percent / pyridine / 21 h / 20 °C 3: 70 percent / TBAF / tetrahydrofuran / 18 h / 40 °C 4: 75 percent / Pd(PPh3)2Cl2; CuI; Et3N / 3.5 h / 20 °C 5: 73 percent / TsNHNH2; NaOAc / 1,2-dimethoxy-ethane; H2O / 4 h / Heating 6: 57 percent / aq. HCl / methanol; tetrahydrofuran / 15 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 68, # 5 p. 1771 - 1779
反应条件
1: PCC 2: 74 percent / InBr3 / ethyl acetate / 18 h / 20 °C 3: 89 percent / pyridine / 21 h / 20 °C 4: 70 percent / TBAF / tetrahydrofuran / 18 h / 40 °C 5: 75 percent / Pd(PPh3)2Cl2; CuI; Et3N / 3.5 h / 20 °C 6: 73 percent / TsNHNH2; NaOAc / 1,2-dimethoxy-ethane; H2O / 4 h / Heating 7: 57 percent / aq. HCl / methanol; tetrahydrofuran / 15 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 68, # 5 p. 1771 - 1779
反应条件
1.1: i-Pr2NH; BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C 1.2: 54 percent / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 19 h 2.1: m-CPBA / CH2Cl2 / 0.5 h / 0 °C 3.1: 0.191 g / toluene / 1 h / Heating 4.1: 89 percent / HF*pyridine / tetrahydrofuran / 25 h / 20 °C 5.1: 75 percent / Pd(PPh3)2Cl2; CuI; Et3N / 3.5 h / 20 °C 6.1: 73 percent / TsNHNH2; NaOAc / 1,2-dimethoxy-ethane; H2O / 4 h / Heating 7.1: 57 percent / aq. HCl / methanol; tetrahydrofuran / 15 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 68, # 5 p. 1771 - 1779
反应条件
1: 89 percent / HF*pyridine / tetrahydrofuran / 25 h / 20 °C 2: 75 percent / Pd(PPh3)2Cl2; CuI; Et3N / 3.5 h / 20 °C 3: 73 percent / TsNHNH2; NaOAc / 1,2-dimethoxy-ethane; H2O / 4 h / Heating 4: 57 percent / aq. HCl / methanol; tetrahydrofuran / 15 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 68, # 5 p. 1771 - 1779
反应条件
1.1: 2,6-lutidine / CH2Cl2 / 0.5 h / -78 °C 2.1: 0.85 g / 2,6-lutidine / CH2Cl2 / 1.5 h / cooling 3.1: i-Pr2NH; BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C 3.2: 54 percent / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 19 h 4.1: m-CPBA / CH2Cl2 / 0.5 h / 0 °C 5.1: 0.191 g / toluene / 1 h / Heating 6.1: 89 percent / HF*pyridine / tetrahydrofuran / 25 h / 20 °C 7.1: 75 percent / Pd(PPh3)2Cl2; CuI; Et3N / 3.5 h / 20 °C 8.1: 73 percent / TsNHNH2; NaOAc / 1,2-dimethoxy-ethane; H2O / 4 h / Heating 9.1: 57 percent / aq. HCl / methanol; tetrahydrofuran / 15 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 68, # 5 p. 1771 - 1779
反应条件
1.1: 93 percent / Dowex 50WX2-200 resin / methanol / 2 h 2.1: 2,6-lutidine / CH2Cl2 / 0.5 h / -78 °C 3.1: 0.85 g / 2,6-lutidine / CH2Cl2 / 1.5 h / cooling 4.1: i-Pr2NH; BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C 4.2: 54 percent / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 19 h 5.1: m-CPBA / CH2Cl2 / 0.5 h / 0 °C 6.1: 0.191 g / toluene / 1 h / Heating 7.1: 89 percent / HF*pyridine / tetrahydrofuran / 25 h / 20 °C 8.1: 75 percent / Pd(PPh3)2Cl2; CuI; Et3N / 3.5 h / 20 °C 9.1: 73 percent / TsNHNH2; NaOAc / 1,2-dimethoxy-ethane; H2O / 4 h / Heating 10.1: 57 percent / aq. HCl / methanol; tetrahydrofuran / 15 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 68, # 5 p. 1771 - 1779
反应条件
1: 75 percent / Pd(PPh3)2Cl2; CuI; Et3N / 3.5 h / 20 °C 2: 73 percent / TsNHNH2; NaOAc / 1,2-dimethoxy-ethane; H2O / 4 h / Heating 3: 57 percent / aq. HCl / methanol; tetrahydrofuran / 15 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 68, # 5 p. 1771 - 1779
反应条件
1.1: 0.85 g / 2,6-lutidine / CH2Cl2 / 1.5 h / cooling 2.1: i-Pr2NH; BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C 2.2: 54 percent / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 19 h 3.1: m-CPBA / CH2Cl2 / 0.5 h / 0 °C 4.1: 0.191 g / toluene / 1 h / Heating 5.1: 89 percent / HF*pyridine / tetrahydrofuran / 25 h / 20 °C 6.1: 75 percent / Pd(PPh3)2Cl2; CuI; Et3N / 3.5 h / 20 °C 7.1: 73 percent / TsNHNH2; NaOAc / 1,2-dimethoxy-ethane; H2O / 4 h / Heating 8.1: 57 percent / aq. HCl / methanol; tetrahydrofuran / 15 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 68, # 5 p. 1771 - 1779
反应条件
1.1: i-Pr2NH; BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C 1.2: 54 percent / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 19 h 2.1: m-CPBA / CH2Cl2 / 0.5 h / 0 °C 3.1: 0.191 g / toluene / 1 h / Heating 4.1: 89 percent / HF*pyridine / tetrahydrofuran / 25 h / 20 °C 5.1: 75 percent / Pd(PPh3)2Cl2; CuI; Et3N / 3.5 h / 20 °C 6.1: 73 percent / TsNHNH2; NaOAc / 1,2-dimethoxy-ethane; H2O / 4 h / Heating 7.1: 57 percent / aq. HCl / methanol; tetrahydrofuran / 15 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 68, # 5 p. 1771 - 1779
