12(S)-HYDROXY-(5Z,8Z,10E,14Z)-EICOSATETRAENOIC ACID合成路线 （共 60 条）
反应条件
1: 1. n-butyllithium / 1. DME, hexane, -78 deg C, 75 min 2. 10 deg C, 23 h 2: 92 percent / H2 / NaBH4, Ni(Ac)2*4H2O, ethylene diamine / ethanol / 2 h 3: 73 percent / NEt3 / diethyl ether / 0 °C 4: 86 percent / NaI, K2CO3 / acetone / 168 h / 35 °C 5: 76 percent / K2CO3 / acetonitrile / 72 h / 45 °C 6: 1. n-butyllithium / 1. -20 deg C, THF, hexane 2. a. -80 deg C, b. warm up to -10 deg C, 75 min c. 90 min, -10 deg C 7: 68 percent / aq. oxalic acid / tetrahydrofuran / 1 h / Ambient temperature 8: 86 percent / K2CO3 / 1 h / 23 °C 9: 13.5 mg / tetrabutylammonium fluoride / tetrahydrofuran / 25 h / 20 °C 10: aq. NaOH / methanol / 5 h / Ambient temperature View Scheme
参考文献
Bulletin de la Societe Chimique de France, , # 2 p. 298 - 315
反应条件
1: 92 percent / H2 / NaBH4, Ni(Ac)2*4H2O, ethylene diamine / ethanol / 2 h 2: 73 percent / NEt3 / diethyl ether / 0 °C 3: 86 percent / NaI, K2CO3 / acetone / 168 h / 35 °C 4: 76 percent / K2CO3 / acetonitrile / 72 h / 45 °C 5: 1. n-butyllithium / 1. -20 deg C, THF, hexane 2. a. -80 deg C, b. warm up to -10 deg C, 75 min c. 90 min, -10 deg C 6: 68 percent / aq. oxalic acid / tetrahydrofuran / 1 h / Ambient temperature 7: 86 percent / K2CO3 / 1 h / 23 °C 8: 13.5 mg / tetrabutylammonium fluoride / tetrahydrofuran / 25 h / 20 °C 9: aq. NaOH / methanol / 5 h / Ambient temperature View Scheme
参考文献
Bulletin de la Societe Chimique de France, , # 2 p. 298 - 315
反应条件
1: 82 percent / HMPA / tetrahydrofuran / 0.5 h / -78 °C 2: 90 percent / pyridinium p-toluenesulfonate / methanol / 1.5 h / 20 °C 3: 90 percent / 1N LiOH; CO2 / methanol; tetrahydrofuran / 2.5 h / 0 °C View Scheme
参考文献
Tetrahedron, , vol. 57, # 1 p. 25 - 37
反应条件
1: 91 percent / Na2CO3, Pb(OAc)4 / CH2Cl2 / 0.25 h / -78 °C 2: 55 percent / toluene / 3 h / 80 °C 3: lithium hexamethyldisilazane (LiHMDS) / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 - 0 °C 4: NaHCO3 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / Ambient temperature 5: 74 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature 6: 95 percent / LiOH / 1,2-dimethoxy-ethane; H2O / Ambient temperature View Scheme
参考文献
Journal of Organic Chemistry, , vol. 51, # 6 p. 789 - 793
反应条件
1: 83 percent / aq. TFA / tetrahydrofuran / Ambient temperature 2: 91 percent / Na2CO3, Pb(OAc)4 / CH2Cl2 / 0.25 h / -78 °C 3: 55 percent / toluene / 3 h / 80 °C 4: lithium hexamethyldisilazane (LiHMDS) / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 - 0 °C 5: NaHCO3 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / Ambient temperature 6: 74 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature 7: 95 percent / LiOH / 1,2-dimethoxy-ethane; H2O / Ambient temperature View Scheme
参考文献
Journal of Organic Chemistry, , vol. 51, # 6 p. 789 - 793
反应条件
1: NaHCO3 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / Ambient temperature 2: 74 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature 3: 95 percent / LiOH / 1,2-dimethoxy-ethane; H2O / Ambient temperature View Scheme
参考文献
Journal of Organic Chemistry, , vol. 51, # 6 p. 789 - 793
反应条件
1: 74 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature 2: 95 percent / LiOH / 1,2-dimethoxy-ethane; H2O / Ambient temperature View Scheme
参考文献
Journal of Organic Chemistry, , vol. 51, # 6 p. 789 - 793
反应条件
1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C 2: 82 percent / HMPA / tetrahydrofuran / 0.5 h / -78 °C 3: 90 percent / pyridinium p-toluenesulfonate / methanol / 1.5 h / 20 °C 4: 90 percent / 1N LiOH; CO2 / methanol; tetrahydrofuran / 2.5 h / 0 °C View Scheme
参考文献
Tetrahedron, , vol. 57, # 1 p. 25 - 37
反应条件
1: 66 percent / imidazole; Et3N / dimethylformamide / 0.5 h / 0 °C 2: H2; Lindlar catalyst; Et3N / hexane / 1 h 3: oxalyl chloride; DMSO; Et3N / CH2Cl2 / 0.67 h / -70 - -40 °C 4: benzene / 2 h / 60 °C 5: 82 percent / HMPA / tetrahydrofuran / 0.5 h / -78 °C 6: 90 percent / pyridinium p-toluenesulfonate / methanol / 1.5 h / 20 °C 7: 90 percent / 1N LiOH; CO2 / methanol; tetrahydrofuran / 2.5 h / 0 °C View Scheme
参考文献
Tetrahedron, , vol. 57, # 1 p. 25 - 37
反应条件
1: H2; Lindlar catalyst; Et3N / hexane / 1 h 2: oxalyl chloride; DMSO; Et3N / CH2Cl2 / 0.67 h / -70 - -40 °C 3: benzene / 2 h / 60 °C 4: 82 percent / HMPA / tetrahydrofuran / 0.5 h / -78 °C 5: 90 percent / pyridinium p-toluenesulfonate / methanol / 1.5 h / 20 °C 6: 90 percent / 1N LiOH; CO2 / methanol; tetrahydrofuran / 2.5 h / 0 °C View Scheme
参考文献
Tetrahedron, , vol. 57, # 1 p. 25 - 37
