(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
1.1: 86 percent / I2; Ph3P; imidazole / CH2Cl2 / 1 h / 20 °C 2.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 3.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 3.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 4.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 5.1: 83 percent / AcCl / methanol; CH2Cl2 / 2 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 65, # 19 p. 6035 - 6051
反应条件
1.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 2.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 2.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 3.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 4.1: 83 percent / AcCl / methanol; CH2Cl2 / 2 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 65, # 19 p. 6035 - 6051
反应条件
1: 0.5 h / 20 °C 2: Pd(PPh3)4; water / tetrahydrofuran / 2 h / 20 °C 3: AgNO3/SiO2 / hexane; CH2Cl2 / 2 h 4: KCN / methanol / 0.33 h View Scheme
参考文献
Journal of the American Chemical Society, , vol. 127, # 31 p. 10818 - 10819
反应条件
1: TBAF / dimethylformamide; tetrahydrofuran / 6 h / 90 °C 2: 0.5 h / 20 °C 3: Pd(PPh3)4; water / tetrahydrofuran / 2 h / 20 °C 4: AgNO3/SiO2 / hexane; CH2Cl2 / 2 h 5: KCN / methanol / 0.33 h View Scheme
参考文献
Journal of the American Chemical Society, , vol. 127, # 31 p. 10818 - 10819
反应条件
1: 80 percent / InBr3 / ethyl acetate / -78 - 20 °C 2: 82 percent / pyridine 3: H2 / Pd/C 4: PCC 5: 74 percent / InBr3 / ethyl acetate / 18 h / 20 °C 6: 89 percent / pyridine / 21 h / 20 °C 7: 70 percent / TBAF / tetrahydrofuran / 18 h / 40 °C 8: 75 percent / Pd(PPh3)2Cl2; CuI; Et3N / 3.5 h / 20 °C 9: 73 percent / TsNHNH2; NaOAc / 1,2-dimethoxy-ethane; H2O / 4 h / Heating 10: 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: 82 percent / pyridine 2: H2 / Pd/C 3: PCC 4: 74 percent / InBr3 / ethyl acetate / 18 h / 20 °C 5: 89 percent / pyridine / 21 h / 20 °C 6: 70 percent / TBAF / tetrahydrofuran / 18 h / 40 °C 7: 75 percent / Pd(PPh3)2Cl2; CuI; Et3N / 3.5 h / 20 °C 8: 73 percent / TsNHNH2; NaOAc / 1,2-dimethoxy-ethane; H2O / 4 h / Heating 9: 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: H2 / Pd/C 2: PCC 3: 74 percent / InBr3 / ethyl acetate / 18 h / 20 °C 4: 89 percent / pyridine / 21 h / 20 °C 5: 70 percent / TBAF / tetrahydrofuran / 18 h / 40 °C 6: 75 percent / Pd(PPh3)2Cl2; CuI; Et3N / 3.5 h / 20 °C 7: 73 percent / TsNHNH2; NaOAc / 1,2-dimethoxy-ethane; H2O / 4 h / Heating 8: 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: propionic acid / xylene / 2.5 h / Heating 2.1: AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 16 h / 0 °C 3.1: KOH / H2O; methanol / 2 h / 60 °C 4.1: 13.52 g / TsOH / CH2Cl2 5.1: 94 percent / imidazole / dimethylformamide / 16 h / 20 °C 6.1: 98 percent / H2; propionic acid / methanol / 16 h 7.1: PCC; Celite / CH2Cl2 / 2 h / 20 °C 8.1: NaHMDS / hexamethylphosphoric acid triamide; tetrahydrofuran / -78 °C 8.2: 76 percent / hexamethylphosphoric acid triamide; tetrahydrofuran / -78 - 20 °C 9.1: 88 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 10.1: 64 percent / Re2O7; 2,6-lutidine / CH2Cl2 / 20 °C 11.1: 94 percent / Et3N / CH2Cl2 / 0.5 h / -30 °C 12.1: 90 percent / TsOH / H2O; methanol / 16 h / 20 °C 13.1: 81 percent / pyridine / 3 h / Heating 14.1: 100 percent / LiAlH4 / diethyl ether / 2 h / Heating 15.1: diisopropylethylamine; DMAP / CH2Cl2 / 6 h / 20 °C 16.1: 508 mg / diisopropylethylamine / CH2Cl2 / 12 h 17.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 18.1: 86 percent / I2; Ph3P; imidazole / CH2Cl2 / 1 h / 20 °C 19.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 20.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 20.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 21.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 22.1: 83 percent / AcCl / methanol; CH2Cl2 / 2 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 65, # 19 p. 6035 - 6051
反应条件
1.1: AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 16 h / 0 °C 2.1: KOH / H2O; methanol / 2 h / 60 °C 3.1: 13.52 g / TsOH / CH2Cl2 4.1: 94 percent / imidazole / dimethylformamide / 16 h / 20 °C 5.1: 98 percent / H2; propionic acid / methanol / 16 h 6.1: PCC; Celite / CH2Cl2 / 2 h / 20 °C 7.1: NaHMDS / hexamethylphosphoric acid triamide; tetrahydrofuran / -78 °C 7.2: 76 percent / hexamethylphosphoric acid triamide; tetrahydrofuran / -78 - 20 °C 8.1: 88 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 9.1: 64 percent / Re2O7; 2,6-lutidine / CH2Cl2 / 20 °C 10.1: 94 percent / Et3N / CH2Cl2 / 0.5 h / -30 °C 11.1: 90 percent / TsOH / H2O; methanol / 16 h / 20 °C 12.1: 81 percent / pyridine / 3 h / Heating 13.1: 100 percent / LiAlH4 / diethyl ether / 2 h / Heating 14.1: diisopropylethylamine; DMAP / CH2Cl2 / 6 h / 20 °C 15.1: 508 mg / diisopropylethylamine / CH2Cl2 / 12 h 16.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 17.1: 86 percent / I2; Ph3P; imidazole / CH2Cl2 / 1 h / 20 °C 18.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 19.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 19.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 20.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 21.1: 83 percent / AcCl / methanol; CH2Cl2 / 2 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 65, # 19 p. 6035 - 6051
反应条件
1.1: NaHMDS / hexamethylphosphoric acid triamide; tetrahydrofuran / -78 °C 1.2: 76 percent / hexamethylphosphoric acid triamide; tetrahydrofuran / -78 - 20 °C 2.1: 88 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 3.1: 64 percent / Re2O7; 2,6-lutidine / CH2Cl2 / 20 °C 4.1: 94 percent / Et3N / CH2Cl2 / 0.5 h / -30 °C 5.1: 90 percent / TsOH / H2O; methanol / 16 h / 20 °C 6.1: 81 percent / pyridine / 3 h / Heating 7.1: 100 percent / LiAlH4 / diethyl ether / 2 h / Heating 8.1: diisopropylethylamine; DMAP / CH2Cl2 / 6 h / 20 °C 9.1: 508 mg / diisopropylethylamine / CH2Cl2 / 12 h 10.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 11.1: 86 percent / I2; Ph3P; imidazole / CH2Cl2 / 1 h / 20 °C 12.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 13.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 13.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 14.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 15.1: 83 percent / AcCl / methanol; CH2Cl2 / 2 h / 20 °C View Scheme
参考文献
Journal of Organic Chemistry, , vol. 65, # 19 p. 6035 - 6051
