5-乙基-5,6-二氢-6-[(2R,3S,4R,5S,7E)-2-羟基-4-甲氧基-3,5-二甲基-7-壬烯-1-基]-,(5R,6R)-2H-吡喃-2-酮合成路线 （共 102 条）
反应条件
1: 76 mg / SmI2 / tetrahydrofuran; methanol / 14 h / -16 °C 2: 97 percent / NEt3; DMAP / CH2Cl2 / 14 h / 20 °C 3: 82 percent / DDQ / CH2Cl2; H2O / 0.25 h 4: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 0.42 h 5: 130 mg / diisopropylamine; n-BuLi / tetrahydrofuran; methyl acetate / 1 h / -78 - 20 °C 6: 86 percent / aq. HCl / methanol / 12 h / Heating View Scheme
参考文献
Organic letters, , vol. 3, # 5 p. 707 - 710
反应条件
1: 97 percent / NEt3; DMAP / CH2Cl2 / 14 h / 20 °C 2: 82 percent / DDQ / CH2Cl2; H2O / 0.25 h 3: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 0.42 h 4: 130 mg / diisopropylamine; n-BuLi / tetrahydrofuran; methyl acetate / 1 h / -78 - 20 °C 5: 86 percent / aq. HCl / methanol / 12 h / Heating View Scheme
参考文献
Organic letters, , vol. 3, # 5 p. 707 - 710
反应条件
1: 82 percent / DDQ / CH2Cl2; H2O / 0.25 h 2: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 0.42 h 3: 130 mg / diisopropylamine; n-BuLi / tetrahydrofuran; methyl acetate / 1 h / -78 - 20 °C 4: 86 percent / aq. HCl / methanol / 12 h / Heating View Scheme
参考文献
Organic letters, , vol. 3, # 5 p. 707 - 710
反应条件
1: Pb(OAc)4, K2CO3 / benzene / Ambient temperature 2: 63 percent / KHMDS, 18-crown-6 / tetrahydrofuran / -78 °C 3: DIBAL-H / CH2Cl2 / -78 °C 4: 2,6-lutidine / CH2Cl2 / 0 °C 5: 56 percent / tert-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 deg C, 10 min, 2.) -78 deg C, 30 min 6: NCS, aq. AgNO3, 2,4,6-collidine / acetonitrile / 0.02 h / 0 °C 7: 65 percent / NaBH(OAc)3 / acetonitrile; acetic acid / 5 h / 0 °C 8: 82 percent / TBAF / tetrahydrofuran / Ambient temperature 9: 87 percent / MnO2 / CH2Cl2 / 3 h / Ambient temperature View Scheme
参考文献
Chemical Communications, , # 11 p. 1043 - 1044
反应条件
1: 56 percent / tert-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 deg C, 10 min, 2.) -78 deg C, 30 min 2: NCS, aq. AgNO3, 2,4,6-collidine / acetonitrile / 0.02 h / 0 °C 3: 65 percent / NaBH(OAc)3 / acetonitrile; acetic acid / 5 h / 0 °C 4: 82 percent / TBAF / tetrahydrofuran / Ambient temperature 5: 87 percent / MnO2 / CH2Cl2 / 3 h / Ambient temperature View Scheme
参考文献
Chemical Communications, , # 11 p. 1043 - 1044
反应条件
1: 71 percent / Ph3P, diethyl azodicarboxylate / toluene / 36 h / Heating 2: 56 percent / tert-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 deg C, 10 min, 2.) -78 deg C, 30 min 3: NCS, aq. AgNO3, 2,4,6-collidine / acetonitrile / 0.02 h / 0 °C 4: 65 percent / NaBH(OAc)3 / acetonitrile; acetic acid / 5 h / 0 °C 5: 82 percent / TBAF / tetrahydrofuran / Ambient temperature 6: 87 percent / MnO2 / CH2Cl2 / 3 h / Ambient temperature View Scheme
参考文献
Chemical Communications, , # 11 p. 1043 - 1044
反应条件
1: 2,6-lutidine / CH2Cl2 / 0 °C 2: 56 percent / tert-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 deg C, 10 min, 2.) -78 deg C, 30 min 3: NCS, aq. AgNO3, 2,4,6-collidine / acetonitrile / 0.02 h / 0 °C 4: 65 percent / NaBH(OAc)3 / acetonitrile; acetic acid / 5 h / 0 °C 5: 82 percent / TBAF / tetrahydrofuran / Ambient temperature 6: 87 percent / MnO2 / CH2Cl2 / 3 h / Ambient temperature View Scheme
参考文献
Chemical Communications, , # 11 p. 1043 - 1044
反应条件
1: 56 percent / tert-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -78 deg C, 10 min, 2.) -78 deg C, 30 min 2: NCS, aq. AgNO3, 2,4,6-collidine / acetonitrile / 0.02 h / 0 °C 3: 65 percent / NaBH(OAc)3 / acetonitrile; acetic acid / 5 h / 0 °C 4: 82 percent / TBAF / tetrahydrofuran / Ambient temperature 5: 87 percent / MnO2 / CH2Cl2 / 3 h / Ambient temperature View Scheme
参考文献
Chemical Communications, , # 11 p. 1043 - 1044
反应条件
1: 65 percent / NaBH(OAc)3 / acetonitrile; acetic acid / 5 h / 0 °C 2: 82 percent / TBAF / tetrahydrofuran / Ambient temperature 3: 87 percent / MnO2 / CH2Cl2 / 3 h / Ambient temperature View Scheme
参考文献
Chemical Communications, , # 11 p. 1043 - 1044
反应条件
1: NCS, aq. AgNO3, 2,4,6-collidine / acetonitrile / 0.02 h / 0 °C 2: 65 percent / NaBH(OAc)3 / acetonitrile; acetic acid / 5 h / 0 °C 3: 82 percent / TBAF / tetrahydrofuran / Ambient temperature 4: 87 percent / MnO2 / CH2Cl2 / 3 h / Ambient temperature View Scheme
参考文献
Chemical Communications, , # 11 p. 1043 - 1044
