(5Z,8Z,10E,14Z)-12-羟基-5,8,10,14-二十碳四烯酸合成路线 (共 37 条)
反应条件
1: benzene; diethyl ether / -10 - -5 °C
2: Rh(OAc)2 / 1 h / Ambient temperature
3: CeCl3*5H2O, NaBH4 / propan-2-ol; H2O
4: pyridine / 0 °C
5: imidazole / dimethylformamide / Ambient temperature
6: 98 percent / H2, pyridine / Lindlar catalyst / hexane / 10 h / 760 Torr
7: 46 percent / 80percent AcOH / 48 h / Ambient temperature
8: 96 percent / CBr4, bis(1,2-diphenylphosphino)ethane (DIPHOS) / CH2Cl2 / 0.5 h / Ambient temperature
9: 1.) CuI, n-BuLi, 2.) HMPA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, a.) from -78 to 0 deg C, 1 h, b) RT, 1 h
10: 61 percent / H2, pyridine / Lindlar catalyst / hexane / 10 h / 760 Torr
11: tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature
12: LiOH / 1,2-dimethoxy-ethane; H2O / Ambient temperature
View Scheme
参考文献
Leblanc, Yves; Fitzsimmons, Brian J.; Adams, Julian; Perez, Francoise; Rokach, Joshua
Journal of Organic Chemistry, 1986 , vol. 51, # 6 p. 789 - 793
反应条件
1: Rh(OAc)2 / 1 h / Ambient temperature
2: CeCl3*5H2O, NaBH4 / propan-2-ol; H2O
3: pyridine / 0 °C
4: imidazole / dimethylformamide / Ambient temperature
5: 98 percent / H2, pyridine / Lindlar catalyst / hexane / 10 h / 760 Torr
6: 46 percent / 80percent AcOH / 48 h / Ambient temperature
7: 96 percent / CBr4, bis(1,2-diphenylphosphino)ethane (DIPHOS) / CH2Cl2 / 0.5 h / Ambient temperature
8: 1.) CuI, n-BuLi, 2.) HMPA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, a.) from -78 to 0 deg C, 1 h, b) RT, 1 h
9: 61 percent / H2, pyridine / Lindlar catalyst / hexane / 10 h / 760 Torr
10: tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature
11: LiOH / 1,2-dimethoxy-ethane; H2O / Ambient temperature
View Scheme
参考文献
Leblanc, Yves; Fitzsimmons, Brian J.; Adams, Julian; Perez, Francoise; Rokach, Joshua
Journal of Organic Chemistry, 1986 , vol. 51, # 6 p. 789 - 793
反应条件
1: pyridine / 0 °C
2: imidazole / dimethylformamide / Ambient temperature
3: 98 percent / H2, pyridine / Lindlar catalyst / hexane / 10 h / 760 Torr
4: 46 percent / 80percent AcOH / 48 h / Ambient temperature
5: 96 percent / CBr4, bis(1,2-diphenylphosphino)ethane (DIPHOS) / CH2Cl2 / 0.5 h / Ambient temperature
6: 1.) CuI, n-BuLi, 2.) HMPA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, a.) from -78 to 0 deg C, 1 h, b) RT, 1 h
7: 61 percent / H2, pyridine / Lindlar catalyst / hexane / 10 h / 760 Torr
8: tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature
9: LiOH / 1,2-dimethoxy-ethane; H2O / Ambient temperature
View Scheme
参考文献
Leblanc, Yves; Fitzsimmons, Brian J.; Adams, Julian; Perez, Francoise; Rokach, Joshua
Journal of Organic Chemistry, 1986 , vol. 51, # 6 p. 789 - 793
反应条件
1: CeCl3*5H2O, NaBH4 / propan-2-ol; H2O
2: pyridine / 0 °C
3: imidazole / dimethylformamide / Ambient temperature
4: 98 percent / H2, pyridine / Lindlar catalyst / hexane / 10 h / 760 Torr
5: 46 percent / 80percent AcOH / 48 h / Ambient temperature
6: 96 percent / CBr4, bis(1,2-diphenylphosphino)ethane (DIPHOS) / CH2Cl2 / 0.5 h / Ambient temperature
7: 1.) CuI, n-BuLi, 2.) HMPA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, a.) from -78 to 0 deg C, 1 h, b) RT, 1 h
8: 61 percent / H2, pyridine / Lindlar catalyst / hexane / 10 h / 760 Torr
9: tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature
10: LiOH / 1,2-dimethoxy-ethane; H2O / Ambient temperature
View Scheme
参考文献
Leblanc, Yves; Fitzsimmons, Brian J.; Adams, Julian; Perez, Francoise; Rokach, Joshua
Journal of Organic Chemistry, 1986 , vol. 51, # 6 p. 789 - 793
反应条件
1: imidazole / dimethylformamide / Ambient temperature
2: 98 percent / H2, pyridine / Lindlar catalyst / hexane / 10 h / 760 Torr
3: 46 percent / 80percent AcOH / 48 h / Ambient temperature
4: 96 percent / CBr4, bis(1,2-diphenylphosphino)ethane (DIPHOS) / CH2Cl2 / 0.5 h / Ambient temperature
5: 1.) CuI, n-BuLi, 2.) HMPA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, a.) from -78 to 0 deg C, 1 h, b) RT, 1 h
6: 61 percent / H2, pyridine / Lindlar catalyst / hexane / 10 h / 760 Torr
7: tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature
8: LiOH / 1,2-dimethoxy-ethane; H2O / Ambient temperature
View Scheme
参考文献
Leblanc, Yves; Fitzsimmons, Brian J.; Adams, Julian; Perez, Francoise; Rokach, Joshua
Journal of Organic Chemistry, 1986 , vol. 51, # 6 p. 789 - 793
反应条件
1: 61 percent / H2, pyridine / Lindlar catalyst / hexane / 10 h / 760 Torr
2: tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature
3: LiOH / 1,2-dimethoxy-ethane; H2O / Ambient temperature
View Scheme
参考文献
Leblanc, Yves; Fitzsimmons, Brian J.; Adams, Julian; Perez, Francoise; Rokach, Joshua
Journal of Organic Chemistry, 1986 , vol. 51, # 6 p. 789 - 793
反应条件
1: 46 percent / 80percent AcOH / 48 h / Ambient temperature
2: 96 percent / CBr4, bis(1,2-diphenylphosphino)ethane (DIPHOS) / CH2Cl2 / 0.5 h / Ambient temperature
3: 1.) CuI, n-BuLi, 2.) HMPA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, a.) from -78 to 0 deg C, 1 h, b) RT, 1 h
4: 61 percent / H2, pyridine / Lindlar catalyst / hexane / 10 h / 760 Torr
5: tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature
6: LiOH / 1,2-dimethoxy-ethane; H2O / Ambient temperature
View Scheme
参考文献
Leblanc, Yves; Fitzsimmons, Brian J.; Adams, Julian; Perez, Francoise; Rokach, Joshua
Journal of Organic Chemistry, 1986 , vol. 51, # 6 p. 789 - 793
反应条件
1: 98 percent / H2, pyridine / Lindlar catalyst / hexane / 10 h / 760 Torr
2: 46 percent / 80percent AcOH / 48 h / Ambient temperature
3: 96 percent / CBr4, bis(1,2-diphenylphosphino)ethane (DIPHOS) / CH2Cl2 / 0.5 h / Ambient temperature
4: 1.) CuI, n-BuLi, 2.) HMPA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, a.) from -78 to 0 deg C, 1 h, b) RT, 1 h
5: 61 percent / H2, pyridine / Lindlar catalyst / hexane / 10 h / 760 Torr
6: tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature
7: LiOH / 1,2-dimethoxy-ethane; H2O / Ambient temperature
View Scheme
参考文献
Leblanc, Yves; Fitzsimmons, Brian J.; Adams, Julian; Perez, Francoise; Rokach, Joshua
Journal of Organic Chemistry, 1986 , vol. 51, # 6 p. 789 - 793
反应条件
1: 96 percent / CBr4, bis(1,2-diphenylphosphino)ethane (DIPHOS) / CH2Cl2 / 0.5 h / Ambient temperature
2: 1.) CuI, n-BuLi, 2.) HMPA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, a.) from -78 to 0 deg C, 1 h, b) RT, 1 h
3: 61 percent / H2, pyridine / Lindlar catalyst / hexane / 10 h / 760 Torr
4: tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature
5: LiOH / 1,2-dimethoxy-ethane; H2O / Ambient temperature
View Scheme
参考文献
Leblanc, Yves; Fitzsimmons, Brian J.; Adams, Julian; Perez, Francoise; Rokach, Joshua
Journal of Organic Chemistry, 1986 , vol. 51, # 6 p. 789 - 793
反应条件
1: 1.) CuI, n-BuLi, 2.) HMPA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, a.) from -78 to 0 deg C, 1 h, b) RT, 1 h
2: 61 percent / H2, pyridine / Lindlar catalyst / hexane / 10 h / 760 Torr
3: tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature
4: LiOH / 1,2-dimethoxy-ethane; H2O / Ambient temperature
View Scheme
参考文献
Leblanc, Yves; Fitzsimmons, Brian J.; Adams, Julian; Perez, Francoise; Rokach, Joshua
Journal of Organic Chemistry, 1986 , vol. 51, # 6 p. 789 - 793