4-羟基-3-[(1E,3E)-5-羟基-4-甲基戊-1,3-二烯基]-7-甲氧基-2,3,8-三甲基-2H-苯并[g][1]苯并呋喃-6,9-二酮合成路线 （共 10 条）
反应条件
4 A molecular sieve; tetrabutyl ammonium fluoride in tetrahydrofuran
T=0°C; 0.5 h;
参考文献
Trost, Barry M.; Thiel, Oliver R.; Tsui, Hon-Chung
Journal of the American Chemical Society, 2003 , vol. 125, # 43 p. 13155 - 13164
反应条件
1.1: Pd2(dba)3*CHCl3; (1R,2R)-bis[2-(di-Ph-phosphinyl)-benzamino]-1,2-di-Ph-ethane / CH2Cl2 / 4 h / 20 °C
2.1: PdCl2(CH3CN)2; 1,2,2,6,6-pentamethylpiperidine; formic acid / dimethylformamide / 6 h / 50 °C
3.1: 96 percent / TEA / CH2Cl2
4.1: 92 percent / NBS / tetrahydrofuran / 20 °C
5.1: DIBAL-H / CH2Cl2 / -78 °C
6.1: LHMDS / tetrahydrofuran / 0.5 h / 0 °C
6.2: 368 mg / tetrahydrofuran / 20 °C
7.1: DIBAL-H / CH2Cl2 / 2 h / -78 °C
8.1: 910 mg / imidazole / CH2Cl2 / 2 h / Heating
9.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
9.2: tetrahydrofuran; hexane / 1 h / -78 °C
10.1: 98 mg / aq. oxalic acid / tetrahydrofuran / 0.17 h
11.1: toluene / 3.5 h / 110 °C
11.2: 64 percent / air / toluene / 2 h / 20 °C
12.1: 65 percent / 4A molecular sieves; TBAF / tetrahydrofuran / 0.5 h / 0 °C
View Scheme
参考文献
Trost, Barry M.; Thiel, Oliver R.; Tsui, Hon-Chung
Journal of the American Chemical Society, 2003 , vol. 125, # 43 p. 13155 - 13164
反应条件
1.1: 96 percent / TEA / CH2Cl2
2.1: 92 percent / NBS / tetrahydrofuran / 20 °C
3.1: DIBAL-H / CH2Cl2 / -78 °C
4.1: LHMDS / tetrahydrofuran / 0.5 h / 0 °C
4.2: 368 mg / tetrahydrofuran / 20 °C
5.1: DIBAL-H / CH2Cl2 / 2 h / -78 °C
6.1: 910 mg / imidazole / CH2Cl2 / 2 h / Heating
7.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
7.2: tetrahydrofuran; hexane / 1 h / -78 °C
8.1: 98 mg / aq. oxalic acid / tetrahydrofuran / 0.17 h
9.1: toluene / 3.5 h / 110 °C
9.2: 64 percent / air / toluene / 2 h / 20 °C
10.1: 65 percent / 4A molecular sieves; TBAF / tetrahydrofuran / 0.5 h / 0 °C
View Scheme
参考文献
Trost, Barry M.; Thiel, Oliver R.; Tsui, Hon-Chung
Journal of the American Chemical Society, 2003 , vol. 125, # 43 p. 13155 - 13164
反应条件
1.1: 92 percent / NBS / tetrahydrofuran / 20 °C
2.1: DIBAL-H / CH2Cl2 / -78 °C
3.1: LHMDS / tetrahydrofuran / 0.5 h / 0 °C
3.2: 368 mg / tetrahydrofuran / 20 °C
4.1: DIBAL-H / CH2Cl2 / 2 h / -78 °C
5.1: 910 mg / imidazole / CH2Cl2 / 2 h / Heating
6.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
6.2: tetrahydrofuran; hexane / 1 h / -78 °C
7.1: 98 mg / aq. oxalic acid / tetrahydrofuran / 0.17 h
8.1: toluene / 3.5 h / 110 °C
8.2: 64 percent / air / toluene / 2 h / 20 °C
9.1: 65 percent / 4A molecular sieves; TBAF / tetrahydrofuran / 0.5 h / 0 °C
View Scheme
参考文献
Trost, Barry M.; Thiel, Oliver R.; Tsui, Hon-Chung
Journal of the American Chemical Society, 2003 , vol. 125, # 43 p. 13155 - 13164
反应条件
1.1: LHMDS / tetrahydrofuran / 0.5 h / 0 °C
1.2: 368 mg / tetrahydrofuran / 20 °C
2.1: DIBAL-H / CH2Cl2 / 2 h / -78 °C
3.1: 910 mg / imidazole / CH2Cl2 / 2 h / Heating
4.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
4.2: tetrahydrofuran; hexane / 1 h / -78 °C
5.1: 98 mg / aq. oxalic acid / tetrahydrofuran / 0.17 h
6.1: toluene / 3.5 h / 110 °C
6.2: 64 percent / air / toluene / 2 h / 20 °C
7.1: 65 percent / 4A molecular sieves; TBAF / tetrahydrofuran / 0.5 h / 0 °C
View Scheme
参考文献
Trost, Barry M.; Thiel, Oliver R.; Tsui, Hon-Chung
Journal of the American Chemical Society, 2003 , vol. 125, # 43 p. 13155 - 13164
反应条件
1.1: DIBAL-H / CH2Cl2 / -78 °C
2.1: LHMDS / tetrahydrofuran / 0.5 h / 0 °C
2.2: 368 mg / tetrahydrofuran / 20 °C
3.1: DIBAL-H / CH2Cl2 / 2 h / -78 °C
4.1: 910 mg / imidazole / CH2Cl2 / 2 h / Heating
5.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
5.2: tetrahydrofuran; hexane / 1 h / -78 °C
6.1: 98 mg / aq. oxalic acid / tetrahydrofuran / 0.17 h
7.1: toluene / 3.5 h / 110 °C
7.2: 64 percent / air / toluene / 2 h / 20 °C
8.1: 65 percent / 4A molecular sieves; TBAF / tetrahydrofuran / 0.5 h / 0 °C
View Scheme
参考文献
Trost, Barry M.; Thiel, Oliver R.; Tsui, Hon-Chung
Journal of the American Chemical Society, 2003 , vol. 125, # 43 p. 13155 - 13164
反应条件
1.1: toluene / 3.5 h / 110 °C
1.2: 64 percent / air / toluene / 2 h / 20 °C
2.1: 65 percent / 4A molecular sieves; TBAF / tetrahydrofuran / 0.5 h / 0 °C
View Scheme
参考文献
Trost, Barry M.; Thiel, Oliver R.; Tsui, Hon-Chung
Journal of the American Chemical Society, 2003 , vol. 125, # 43 p. 13155 - 13164
反应条件
potassium carbonate in methanol
参考文献
Dormer, Peter G.; Smith, Amos B.; Funayama, Shinji; Omura, Satoshi
Tetrahedron Letters, 1992 , vol. 33, # 13 p. 1717 - 1720
反应条件
1: 17 percent / Martin sulfurane / tetrahydrofuran / 0 - 5 °C
2: 41 percent / K2CO3 / methanol
View Scheme
参考文献
Dormer, Peter G.; Smith, Amos B.; Funayama, Shinji; Omura, Satoshi
Tetrahedron Letters, 1992 , vol. 33, # 13 p. 1717 - 1720
反应条件
1: 90 percent / Et3N / tetrahydrofuran / 0 - 5 °C
2: 17 percent / Martin sulfurane / tetrahydrofuran / 0 - 5 °C
3: 41 percent / K2CO3 / methanol
View Scheme
参考文献
Dormer, Peter G.; Smith, Amos B.; Funayama, Shinji; Omura, Satoshi
Tetrahedron Letters, 1992 , vol. 33, # 13 p. 1717 - 1720
