2-巴豆酰氧基甲基-(4R,5R,6R)-4,5,6-三羟基环己-2-烯酮合成路线 （共 31 条）
反应条件
water; trifluoroacetic acid
Hydrolysis;
参考文献
Huntley, C. Frederick M.; Wood, Harold B.; Ganem, Bruce
Tetrahedron Letters, 2000 , vol. 41, # 13 p. 2031 - 2034
反应条件
trifluoroacetic acid
T=-20°C; 7 h;
参考文献
Takahashi, Tamiko; Yamakoshi, Yoko; Okayama, Kazuya; Yamada, Junko; Ge, Wei-Ying; Koizumi, Toru
Heterocycles, 2002 , vol. 56, # 1-2 p. 209 - 220
反应条件
1: 96 percent / methanol / 1 h / 0 °C
2: 1) oxalyl chloride, DMSO, 2) triethylamine / 1) CH2Cl2, 40 min, -60 deg C, 2) 10 min, -60 deg C
3: POCl3, pyridine / Ambient temperature
4: 82 percent / NaBH4 / methanol / 1.5 h / 0 °C
5: 82 percent / OsO4, trimethylamine-N-oxide, pyridine, water / 2-methyl-propan-2-ol / 12 h / Heating
6: 100 percent / pyridine, N,N-dimethylaminopyridine (DMAP) / CH2Cl2 / 12 h / Ambient temperature
7: 86 percent / pyridine, N,N-dimethylaminopyridine (DMAP) / CH2Cl2 / 1) -78 deg C, 1 h, 2) to 0 deg C, 12 h
8: 71 percent / triethylamine, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / CH2Cl2 / 6 h / 0 °C
9: 75 percent / diisobutylaluminium hydride (DIBAL-H) / tetrahydrofuran / 1 h / 0 °C
10: 95 percent / pyridine, N,N-dimethylaminopyridine (DMAP) / CH2Cl2 / 12 h / Ambient temperature
11: 80 percent / pyridinium chlorochromate, 3 Angstroem molecular sieves / CH2Cl2 / 12 h / Ambient temperature
12: 100 percent / 50percent aq. CF3COOH / 4 h / Ambient temperature
View Scheme
参考文献
Shing; Tang
Tetrahedron, 1990 , vol. 46, # 18 p. 6575 - 6584
反应条件
1: 82 percent / NaBH4 / methanol / 1.5 h / 0 °C
2: 82 percent / OsO4, trimethylamine-N-oxide, pyridine, water / 2-methyl-propan-2-ol / 12 h / Heating
3: 100 percent / pyridine, N,N-dimethylaminopyridine (DMAP) / CH2Cl2 / 12 h / Ambient temperature
4: 86 percent / pyridine, N,N-dimethylaminopyridine (DMAP) / CH2Cl2 / 1) -78 deg C, 1 h, 2) to 0 deg C, 12 h
5: 71 percent / triethylamine, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / CH2Cl2 / 6 h / 0 °C
6: 75 percent / diisobutylaluminium hydride (DIBAL-H) / tetrahydrofuran / 1 h / 0 °C
7: 95 percent / pyridine, N,N-dimethylaminopyridine (DMAP) / CH2Cl2 / 12 h / Ambient temperature
8: 80 percent / pyridinium chlorochromate, 3 Angstroem molecular sieves / CH2Cl2 / 12 h / Ambient temperature
9: 100 percent / 50percent aq. CF3COOH / 4 h / Ambient temperature
View Scheme
参考文献
Shing; Tang
Tetrahedron, 1990 , vol. 46, # 18 p. 6575 - 6584
反应条件
1: 82 percent / OsO4, trimethylamine-N-oxide, pyridine, water / 2-methyl-propan-2-ol / 12 h / Heating
2: 100 percent / pyridine, N,N-dimethylaminopyridine (DMAP) / CH2Cl2 / 12 h / Ambient temperature
3: 86 percent / pyridine, N,N-dimethylaminopyridine (DMAP) / CH2Cl2 / 1) -78 deg C, 1 h, 2) to 0 deg C, 12 h
4: 71 percent / triethylamine, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / CH2Cl2 / 6 h / 0 °C
5: 75 percent / diisobutylaluminium hydride (DIBAL-H) / tetrahydrofuran / 1 h / 0 °C
6: 95 percent / pyridine, N,N-dimethylaminopyridine (DMAP) / CH2Cl2 / 12 h / Ambient temperature
7: 80 percent / pyridinium chlorochromate, 3 Angstroem molecular sieves / CH2Cl2 / 12 h / Ambient temperature
8: 100 percent / 50percent aq. CF3COOH / 4 h / Ambient temperature
View Scheme
参考文献
Shing; Tang
Tetrahedron, 1990 , vol. 46, # 18 p. 6575 - 6584
反应条件
1: POCl3, pyridine / Ambient temperature
2: 82 percent / NaBH4 / methanol / 1.5 h / 0 °C
3: 82 percent / OsO4, trimethylamine-N-oxide, pyridine, water / 2-methyl-propan-2-ol / 12 h / Heating
4: 100 percent / pyridine, N,N-dimethylaminopyridine (DMAP) / CH2Cl2 / 12 h / Ambient temperature
5: 86 percent / pyridine, N,N-dimethylaminopyridine (DMAP) / CH2Cl2 / 1) -78 deg C, 1 h, 2) to 0 deg C, 12 h
6: 71 percent / triethylamine, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / CH2Cl2 / 6 h / 0 °C
7: 75 percent / diisobutylaluminium hydride (DIBAL-H) / tetrahydrofuran / 1 h / 0 °C
8: 95 percent / pyridine, N,N-dimethylaminopyridine (DMAP) / CH2Cl2 / 12 h / Ambient temperature
9: 80 percent / pyridinium chlorochromate, 3 Angstroem molecular sieves / CH2Cl2 / 12 h / Ambient temperature
10: 100 percent / 50percent aq. CF3COOH / 4 h / Ambient temperature
View Scheme
参考文献
Shing; Tang
Tetrahedron, 1990 , vol. 46, # 18 p. 6575 - 6584
反应条件
1: 95 percent / pyridine, N,N-dimethylaminopyridine (DMAP) / CH2Cl2 / 12 h / Ambient temperature
2: 80 percent / pyridinium chlorochromate, 3 Angstroem molecular sieves / CH2Cl2 / 12 h / Ambient temperature
3: 100 percent / 50percent aq. CF3COOH / 4 h / Ambient temperature
View Scheme
参考文献
Shing; Tang
Tetrahedron, 1990 , vol. 46, # 18 p. 6575 - 6584
反应条件
1: 100 percent / pyridine, N,N-dimethylaminopyridine (DMAP) / CH2Cl2 / 12 h / Ambient temperature
2: 86 percent / pyridine, N,N-dimethylaminopyridine (DMAP) / CH2Cl2 / 1) -78 deg C, 1 h, 2) to 0 deg C, 12 h
3: 71 percent / triethylamine, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / CH2Cl2 / 6 h / 0 °C
4: 75 percent / diisobutylaluminium hydride (DIBAL-H) / tetrahydrofuran / 1 h / 0 °C
5: 95 percent / pyridine, N,N-dimethylaminopyridine (DMAP) / CH2Cl2 / 12 h / Ambient temperature
6: 80 percent / pyridinium chlorochromate, 3 Angstroem molecular sieves / CH2Cl2 / 12 h / Ambient temperature
7: 100 percent / 50percent aq. CF3COOH / 4 h / Ambient temperature
View Scheme
参考文献
Shing; Tang
Tetrahedron, 1990 , vol. 46, # 18 p. 6575 - 6584
反应条件
1: 80 percent / pyridinium chlorochromate, 3 Angstroem molecular sieves / CH2Cl2 / 12 h / Ambient temperature
2: 100 percent / 50percent aq. CF3COOH / 4 h / Ambient temperature
View Scheme
参考文献
Shing; Tang
Tetrahedron, 1990 , vol. 46, # 18 p. 6575 - 6584
反应条件
1: 75 percent / diisobutylaluminium hydride (DIBAL-H) / tetrahydrofuran / 1 h / 0 °C
2: 95 percent / pyridine, N,N-dimethylaminopyridine (DMAP) / CH2Cl2 / 12 h / Ambient temperature
3: 80 percent / pyridinium chlorochromate, 3 Angstroem molecular sieves / CH2Cl2 / 12 h / Ambient temperature
4: 100 percent / 50percent aq. CF3COOH / 4 h / Ambient temperature
View Scheme
参考文献
Shing; Tang
Tetrahedron, 1990 , vol. 46, # 18 p. 6575 - 6584
