(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: 97 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 0.5 h / -78 °C 2.1: 97 percent / DMSO; diisopropylethylamine; SO3*pyridine / CH2Cl2 / 1 h / 0 °C 3.1: BF3*Et2O / tetrahydrofuran; hexane / 0.08 h / -78 °C 3.2: tetrahydrofuran; hexane / 4 h / -78 °C 3.3: 340 mg / aq. H2O2 / tetrahydrofuran; hexane; aq. phosphate buffer / 16 h / 20 °C 4.1: 85 percent / imidazole / various solvent(s) / 72 h / 40 °C 5.1: 4 Angstroem molecular sieves; SnCl4 / CH2Cl2 / -40 °C 6.1: TBAF / dimethylformamide; tetrahydrofuran / 6 h / 90 °C 7.1: 0.5 h / 20 °C 8.1: Pd(PPh3)4; water / tetrahydrofuran / 2 h / 20 °C 9.1: AgNO3/SiO2 / hexane; CH2Cl2 / 2 h 10.1: 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: 85 percent / imidazole / various solvent(s) / 72 h / 40 °C 2: 4 Angstroem molecular sieves; SnCl4 / CH2Cl2 / -40 °C 3: TBAF / dimethylformamide; tetrahydrofuran / 6 h / 90 °C 4: 0.5 h / 20 °C 5: Pd(PPh3)4; water / tetrahydrofuran / 2 h / 20 °C 6: AgNO3/SiO2 / hexane; CH2Cl2 / 2 h 7: 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
1.1: 95 percent / TsOH / acetone / 0.5 h / 20 °C 2.1: 95 percent / H2; Et3N / Lindlar catalyst / hexane; various solvent(s) / 12 h 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
反应条件
1.1: 95 percent / H2; Et3N / Lindlar catalyst / hexane; various solvent(s) / 12 h 2.1: 64 percent / Re2O7; 2,6-lutidine / CH2Cl2 / 20 °C 3.1: 94 percent / Et3N / CH2Cl2 / 0.5 h / -30 °C 4.1: 90 percent / TsOH / H2O; methanol / 16 h / 20 °C 5.1: 81 percent / pyridine / 3 h / Heating 6.1: 100 percent / LiAlH4 / diethyl ether / 2 h / Heating 7.1: diisopropylethylamine; DMAP / CH2Cl2 / 6 h / 20 °C 8.1: 508 mg / diisopropylethylamine / CH2Cl2 / 12 h 9.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 10.1: 86 percent / I2; Ph3P; imidazole / CH2Cl2 / 1 h / 20 °C 11.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 12.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 12.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 13.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 14.1: 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: 64 percent / Re2O7; 2,6-lutidine / CH2Cl2 / 20 °C 2.1: 94 percent / Et3N / CH2Cl2 / 0.5 h / -30 °C 3.1: 90 percent / TsOH / H2O; methanol / 16 h / 20 °C 4.1: 81 percent / pyridine / 3 h / Heating 5.1: 100 percent / LiAlH4 / diethyl ether / 2 h / Heating 6.1: diisopropylethylamine; DMAP / CH2Cl2 / 6 h / 20 °C 7.1: 508 mg / diisopropylethylamine / CH2Cl2 / 12 h 8.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 9.1: 86 percent / I2; Ph3P; imidazole / CH2Cl2 / 1 h / 20 °C 10.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 11.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 11.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 12.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 13.1: 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: 94 percent / Et3N / CH2Cl2 / 0.5 h / -30 °C 2.1: 90 percent / TsOH / H2O; methanol / 16 h / 20 °C 3.1: 81 percent / pyridine / 3 h / Heating 4.1: 100 percent / LiAlH4 / diethyl ether / 2 h / Heating 5.1: diisopropylethylamine; DMAP / CH2Cl2 / 6 h / 20 °C 6.1: 508 mg / diisopropylethylamine / CH2Cl2 / 12 h 7.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 8.1: 86 percent / I2; Ph3P; imidazole / CH2Cl2 / 1 h / 20 °C 9.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 10.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 10.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 11.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 12.1: 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: 81 percent / pyridine / 3 h / Heating 2.1: 100 percent / LiAlH4 / diethyl ether / 2 h / Heating 3.1: diisopropylethylamine; DMAP / CH2Cl2 / 6 h / 20 °C 4.1: 508 mg / diisopropylethylamine / CH2Cl2 / 12 h 5.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 6.1: 86 percent / I2; Ph3P; imidazole / CH2Cl2 / 1 h / 20 °C 7.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 8.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 8.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 9.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 10.1: 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: 90 percent / TsOH / H2O; methanol / 16 h / 20 °C 2.1: 81 percent / pyridine / 3 h / Heating 3.1: 100 percent / LiAlH4 / diethyl ether / 2 h / Heating 4.1: diisopropylethylamine; DMAP / CH2Cl2 / 6 h / 20 °C 5.1: 508 mg / diisopropylethylamine / CH2Cl2 / 12 h 6.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 7.1: 86 percent / I2; Ph3P; imidazole / CH2Cl2 / 1 h / 20 °C 8.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 9.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 9.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 10.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 11.1: 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: diisopropylethylamine; DMAP / CH2Cl2 / 6 h / 20 °C 2.1: 508 mg / diisopropylethylamine / CH2Cl2 / 12 h 3.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 4.1: 86 percent / I2; Ph3P; imidazole / CH2Cl2 / 1 h / 20 °C 5.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 6.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 6.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 7.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 8.1: 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: 100 percent / LiAlH4 / diethyl ether / 2 h / Heating 2.1: diisopropylethylamine; DMAP / CH2Cl2 / 6 h / 20 °C 3.1: 508 mg / diisopropylethylamine / CH2Cl2 / 12 h 4.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 5.1: 86 percent / I2; Ph3P; imidazole / CH2Cl2 / 1 h / 20 °C 6.1: 85 percent / NaHCO3 / acetonitrile / 36 h / 40 °C 7.1: BuLi / hexane; tetrahydrofuran / 0.25 h / cooling 7.2: 60 percent / tetrahydrofuran; hexane / 0.25 h 8.1: 98 percent / H2 / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h 9.1: 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
