20-羟基二十碳-5Z,8Z,11Z,14Z-四烯酸合成路线 （共 34 条）
反应条件
1.1: 96 percent / AgNO3; pyridine / tetrahydrofuran / 12 h 2.1: 92 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / 2 h / -78 - -20 °C 3.1: LiN(SiMe3)2; HMPA / tetrahydrofuran / 1 h / -40 °C 3.2: tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / -78 °C 3.3: 73 percent / methanol; diethyl ether / 0.5 h / 0 °C 4.1: n-Bu4NF / tetrahydrofuran / 3 h / 20 °C 5.1: 90 percent / aq. NaOH / tetrahydrofuran / 20 °C View Scheme
参考文献
Bioorganic & Medicinal Chemistry, , vol. 11, # 13 p. 2802 - 2822
反应条件
1.1: 88 percent / PPh3; CBr4 / CH2Cl2 / 0.67 h / 0 °C 2.1: 89 percent / aq. LiOH / tetrahydrofuran / 12 h / 20 °C 3.1: 92 percent / acetonitrile / 60 h / 85 °C 4.1: LiN(SiMe3)2; HMPA / tetrahydrofuran / 1 h / -40 °C 4.2: tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / -78 °C 4.3: 73 percent / methanol; diethyl ether / 0.5 h / 0 °C 5.1: n-Bu4NF / tetrahydrofuran / 3 h / 20 °C 6.1: 90 percent / aq. NaOH / tetrahydrofuran / 20 °C View Scheme
参考文献
Bioorganic & Medicinal Chemistry, , vol. 11, # 13 p. 2802 - 2822
反应条件
1.1: 92 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / 2 h / -78 - -20 °C 2.1: LiN(SiMe3)2; HMPA / tetrahydrofuran / 1 h / -40 °C 2.2: tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / -78 °C 2.3: 73 percent / methanol; diethyl ether / 0.5 h / 0 °C 3.1: n-Bu4NF / tetrahydrofuran / 3 h / 20 °C 4.1: 90 percent / aq. NaOH / tetrahydrofuran / 20 °C View Scheme
参考文献
Bioorganic & Medicinal Chemistry, , vol. 11, # 13 p. 2802 - 2822
反应条件
1.1: LiN(SiMe3)2; HMPA / tetrahydrofuran / 1 h / -40 °C 1.2: tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / -78 °C 1.3: 73 percent / methanol; diethyl ether / 0.5 h / 0 °C 2.1: n-Bu4NF / tetrahydrofuran / 3 h / 20 °C 3.1: 90 percent / aq. NaOH / tetrahydrofuran / 20 °C View Scheme
参考文献
Bioorganic & Medicinal Chemistry, , vol. 11, # 13 p. 2802 - 2822
反应条件
1.1: 89 percent / aq. LiOH / tetrahydrofuran / 12 h / 20 °C 2.1: 92 percent / acetonitrile / 60 h / 85 °C 3.1: LiN(SiMe3)2; HMPA / tetrahydrofuran / 1 h / -40 °C 3.2: tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / -78 °C 3.3: 73 percent / methanol; diethyl ether / 0.5 h / 0 °C 4.1: n-Bu4NF / tetrahydrofuran / 3 h / 20 °C 5.1: 90 percent / aq. NaOH / tetrahydrofuran / 20 °C View Scheme
参考文献
Bioorganic & Medicinal Chemistry, , vol. 11, # 13 p. 2802 - 2822
反应条件
1.1: 92 percent / acetonitrile / 60 h / 85 °C 2.1: LiN(SiMe3)2; HMPA / tetrahydrofuran / 1 h / -40 °C 2.2: tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / -78 °C 2.3: 73 percent / methanol; diethyl ether / 0.5 h / 0 °C 3.1: n-Bu4NF / tetrahydrofuran / 3 h / 20 °C 4.1: 90 percent / aq. NaOH / tetrahydrofuran / 20 °C View Scheme
参考文献
Bioorganic & Medicinal Chemistry, , vol. 11, # 13 p. 2802 - 2822
反应条件
1: sodium iodide / acetone / 8 h / Heating 2: potassium carbonate / acetonitrile / 10 h / Heating 3: 2.) n-BuLi / tetrahydrofuran / 0.5 h / -78 - -30 °C / 1.) acetonitrile, reflux, 10 h; 2.) THF, from -78 deg C to -30 deg C, 30 min 4: hexamethylphosphoric acid triamide / 1.) -78 deg C, 30 min; 2.) from -78 deg C to 0 deg C, 90 min 5: saponification View Scheme
参考文献
Tetrahedron Letters, , vol. 24, # 1 p. 33 - 36
反应条件
1: potassium carbonate / acetonitrile / 10 h / Heating 2: 2.) n-BuLi / tetrahydrofuran / 0.5 h / -78 - -30 °C / 1.) acetonitrile, reflux, 10 h; 2.) THF, from -78 deg C to -30 deg C, 30 min 3: hexamethylphosphoric acid triamide / 1.) -78 deg C, 30 min; 2.) from -78 deg C to 0 deg C, 90 min 4: saponification View Scheme
参考文献
Tetrahedron Letters, , vol. 24, # 1 p. 33 - 36
反应条件
1: 2.) n-BuLi / tetrahydrofuran / 0.5 h / -78 - -30 °C / 1.) acetonitrile, reflux, 10 h; 2.) THF, from -78 deg C to -30 deg C, 30 min 2: hexamethylphosphoric acid triamide / 1.) -78 deg C, 30 min; 2.) from -78 deg C to 0 deg C, 90 min 3: saponification View Scheme
参考文献
Tetrahedron Letters, , vol. 24, # 1 p. 33 - 36
反应条件
1.1: quinoline; hydrogen / ethyl acetate / 1 h / 20 °C / Inert atmosphere 2.1: lithium hydroxide hydrate / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere 2.2: pH 2 / Inert atmosphere View Scheme
参考文献
Chemistry of Natural Compounds, , vol. 46, # 6 p. 841 - 847
