5,12-二羟基-6,8,14-二十碳三烯酸合成路线 （共 17 条）
反应条件
1: BH3*Me2S / tetrahydrofuran / 2 h / 0 - 23 °C
2: pyridine; CH2Cl2 / 6 h / 24 °C
3: NaOMe / 0.33 h
4: 79 percent / n-BuLi, CuCN / diethyl ether / -70 - -50 °C
5: DIBAL-H / toluene / 3 h / -78 °C
6: toluene / 15 h / 23 °C
7: DMAP, Et3N / pyridine / 26 h / 45 °C
8: DIBAL-H / toluene / 1 h / -78 °C
9: CBr4, PPh3 / CH2Cl2 / 1 h
10: Ph3P / acetonitrile / 6 h
11: 62 percent / 1) n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1) -78 deg C, 1 h, 2) -78 to -50 deg C, 1.5 h
12: 90 percent / n-Bu4NF / tetrahydrofuran / 12 h
13: LiOH / tetrahydrofuran; H2O
View Scheme
参考文献
Yadagiri, Pendri; Lumin, Sun; Falck, J. R.
Tetrahedron Letters, 1989 , vol. 30, # 4 p. 429 - 432
反应条件
1: pyridine; CH2Cl2 / 6 h / 24 °C
2: NaOMe / 0.33 h
3: 79 percent / n-BuLi, CuCN / diethyl ether / -70 - -50 °C
4: DIBAL-H / toluene / 3 h / -78 °C
5: toluene / 15 h / 23 °C
6: DMAP, Et3N / pyridine / 26 h / 45 °C
7: DIBAL-H / toluene / 1 h / -78 °C
8: CBr4, PPh3 / CH2Cl2 / 1 h
9: Ph3P / acetonitrile / 6 h
10: 62 percent / 1) n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1) -78 deg C, 1 h, 2) -78 to -50 deg C, 1.5 h
11: 90 percent / n-Bu4NF / tetrahydrofuran / 12 h
12: LiOH / tetrahydrofuran; H2O
View Scheme
参考文献
Yadagiri, Pendri; Lumin, Sun; Falck, J. R.
Tetrahedron Letters, 1989 , vol. 30, # 4 p. 429 - 432
反应条件
1: DIBAL-H / toluene / 3 h / -78 °C
2: toluene / 15 h / 23 °C
3: DMAP, Et3N / pyridine / 26 h / 45 °C
4: DIBAL-H / toluene / 1 h / -78 °C
5: CBr4, PPh3 / CH2Cl2 / 1 h
6: Ph3P / acetonitrile / 6 h
7: 62 percent / 1) n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1) -78 deg C, 1 h, 2) -78 to -50 deg C, 1.5 h
8: 90 percent / n-Bu4NF / tetrahydrofuran / 12 h
9: LiOH / tetrahydrofuran; H2O
View Scheme
参考文献
Yadagiri, Pendri; Lumin, Sun; Falck, J. R.
Tetrahedron Letters, 1989 , vol. 30, # 4 p. 429 - 432
反应条件
1: Ph3P / acetonitrile / 6 h
2: 62 percent / 1) n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1) -78 deg C, 1 h, 2) -78 to -50 deg C, 1.5 h
3: 90 percent / n-Bu4NF / tetrahydrofuran / 12 h
4: LiOH / tetrahydrofuran; H2O
View Scheme
参考文献
Yadagiri, Pendri; Lumin, Sun; Falck, J. R.
Tetrahedron Letters, 1989 , vol. 30, # 4 p. 429 - 432
反应条件
1: 79 percent / n-BuLi, CuCN / diethyl ether / -70 - -50 °C
2: DIBAL-H / toluene / 3 h / -78 °C
3: toluene / 15 h / 23 °C
4: DMAP, Et3N / pyridine / 26 h / 45 °C
5: DIBAL-H / toluene / 1 h / -78 °C
6: CBr4, PPh3 / CH2Cl2 / 1 h
7: Ph3P / acetonitrile / 6 h
8: 62 percent / 1) n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1) -78 deg C, 1 h, 2) -78 to -50 deg C, 1.5 h
9: 90 percent / n-Bu4NF / tetrahydrofuran / 12 h
10: LiOH / tetrahydrofuran; H2O
View Scheme
参考文献
Yadagiri, Pendri; Lumin, Sun; Falck, J. R.
Tetrahedron Letters, 1989 , vol. 30, # 4 p. 429 - 432
反应条件
1: NaOMe / 0.33 h
2: 79 percent / n-BuLi, CuCN / diethyl ether / -70 - -50 °C
3: DIBAL-H / toluene / 3 h / -78 °C
4: toluene / 15 h / 23 °C
5: DMAP, Et3N / pyridine / 26 h / 45 °C
6: DIBAL-H / toluene / 1 h / -78 °C
7: CBr4, PPh3 / CH2Cl2 / 1 h
8: Ph3P / acetonitrile / 6 h
9: 62 percent / 1) n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1) -78 deg C, 1 h, 2) -78 to -50 deg C, 1.5 h
10: 90 percent / n-Bu4NF / tetrahydrofuran / 12 h
11: LiOH / tetrahydrofuran; H2O
View Scheme
参考文献
Yadagiri, Pendri; Lumin, Sun; Falck, J. R.
Tetrahedron Letters, 1989 , vol. 30, # 4 p. 429 - 432
反应条件
1: DIBAL-H / toluene / 1 h / -78 °C
2: CBr4, PPh3 / CH2Cl2 / 1 h
3: Ph3P / acetonitrile / 6 h
4: 62 percent / 1) n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1) -78 deg C, 1 h, 2) -78 to -50 deg C, 1.5 h
5: 90 percent / n-Bu4NF / tetrahydrofuran / 12 h
6: LiOH / tetrahydrofuran; H2O
View Scheme
参考文献
Yadagiri, Pendri; Lumin, Sun; Falck, J. R.
Tetrahedron Letters, 1989 , vol. 30, # 4 p. 429 - 432
