(3aR,4S,5R,6aS)-4-(叔-丁基二苯基硅烷基氧基)甲基-5-羟基-六氢-2H-环戊[b]呋喃-2-酮合成路线 （共 19 条）
反应条件
sodium hydroxide in methanol
参考文献
Katagiri, Nobuya; Toyota, Akemi; Shiraishi, Takuya; Sato, Hiroshi; Kaneko, Chikara
Tetrahedron Letters, 1992 , vol. 33, # 24 p. 3507 - 3510
反应条件
potassium carbonate in methanol
T=23°C; 1.5 h;
参考文献
Corey, E. J.; Shimoji, Katsuichi
Journal of the American Chemical Society, 1983 , vol. 105, # 6 p. 1662 - 1664
反应条件
1H-imidazole in N,N-dimethyl-formamide
T=-40°C; 2 h;
参考文献
Sato, Ayato; Dodo, Kosuke; Makishima, Makoto; Hashimoto, Yuichi; Sodeoka, Mikiko
Bioorganic and Medicinal Chemistry Letters, 2013 , vol. 23, # 10 p. 3013 - 3017
反应条件
1: 4-(dimethylamino)pyridine / CH2Cl2 / 0.5 h / 0 °C
2: K2CO3 / methanol / 1.5 h / 23 °C
View Scheme
参考文献
Corey, E. J.; Shimoji, Katsuichi
Journal of the American Chemical Society, 1983 , vol. 105, # 6 p. 1662 - 1664
反应条件
1: 1.) trimethylchlorosilane, NaI / 1.) MeCN, 50 deg C, 4 h
2: 4-(dimethylamino)pyridine / CH2Cl2 / 0.5 h / 0 °C
3: K2CO3 / methanol / 1.5 h / 23 °C
View Scheme
参考文献
Corey, E. J.; Shimoji, Katsuichi
Journal of the American Chemical Society, 1983 , vol. 105, # 6 p. 1662 - 1664
反应条件
1: 100 percent / imidazole / dimethylformamide
2: 88 percent / NaOH / methanol
View Scheme
参考文献
Katagiri, Nobuya; Toyota, Akemi; Shiraishi, Takuya; Sato, Hiroshi; Kaneko, Chikara
Tetrahedron Letters, 1992 , vol. 33, # 24 p. 3507 - 3510
反应条件
1: 100 percent / imidazole / dimethylformamide
2: 88 percent / NaOH / methanol
View Scheme
参考文献
Katagiri, Nobuya; Toyota, Akemi; Shiraishi, Takuya; Sato, Hiroshi; Kaneko, Chikara
Tetrahedron Letters, 1992 , vol. 33, # 24 p. 3507 - 3510
反应条件
1.1: CuCN / tetrahydrofuran; diethyl ether / 1 h / -30 °C
1.2: tetrahydrofuran; diethyl ether / 8 h / -12 °C
2.1: pyridinium p-toluenesulfonate / CHCl3 / 12 h / 20 °C
3.1: O3 / CH2Cl2 / -78 °C
3.2: Ph3P / CH2Cl2 / 12 h / 20 °C
4.1: benzene / 7 h / 65 °C
5.1: DIBAL-H / toluene; hexane / 1 h / -78 °C
6.1: PCC; NaOAc; molecular sieves 4 Angstroem / CH2Cl2 / 1 h / 0 °C
7.1: BuLi / tetrahydrofuran; hexane / 0.25 h / 0 °C
7.2: tetrahydrofuran; hexane / 3 h / -78 - 0 °C
8.1: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C
9.1: Dess-Martin reagent / CH2Cl2 / 1 h / 0 °C
10.1: Ni(cod)2; PPh3; i-Bu2-ALAC / toluene / 2 h / 0 °C
11.1: O3 / CH2Cl2 / -78 °C
11.2: PPh3 / CH2Cl2 / 15 h / 20 °C
12.1: PCC; 4 Angstroem molecular sieves; AcONa / CH2Cl2 / 2 h / 0 °C
13.1: Dowex 50wX8 / tetrahydrofuran; H2O / 3 h / 20 °C
14.1: imidazole / dimethylformamide / 2 h / 0 °C
View Scheme
参考文献
Sato; Takimoto; Mori
Chemical and Pharmaceutical Bulletin, 2000 , vol. 48, # 11 p. 1753 - 1760
反应条件
1.1: Ni(cod)2; PPh3; i-Bu2-ALAC / toluene / 2 h / 0 °C
2.1: O3 / CH2Cl2 / -78 °C
2.2: PPh3 / CH2Cl2 / 15 h / 20 °C
3.1: PCC; 4 Angstroem molecular sieves; AcONa / CH2Cl2 / 2 h / 0 °C
4.1: Dowex 50wX8 / tetrahydrofuran; H2O / 3 h / 20 °C
5.1: imidazole / dimethylformamide / 2 h / 0 °C
View Scheme
参考文献
Sato; Takimoto; Mori
Chemical and Pharmaceutical Bulletin, 2000 , vol. 48, # 11 p. 1753 - 1760
反应条件
1.1: pyridinium p-toluenesulfonate / CHCl3 / 12 h / 20 °C
2.1: O3 / CH2Cl2 / -78 °C
2.2: Ph3P / CH2Cl2 / 12 h / 20 °C
3.1: benzene / 7 h / 65 °C
4.1: DIBAL-H / toluene; hexane / 1 h / -78 °C
5.1: PCC; NaOAc; molecular sieves 4 Angstroem / CH2Cl2 / 1 h / 0 °C
6.1: BuLi / tetrahydrofuran; hexane / 0.25 h / 0 °C
6.2: tetrahydrofuran; hexane / 3 h / -78 - 0 °C
7.1: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C
8.1: Dess-Martin reagent / CH2Cl2 / 1 h / 0 °C
9.1: Ni(cod)2; PPh3; i-Bu2-ALAC / toluene / 2 h / 0 °C
10.1: O3 / CH2Cl2 / -78 °C
10.2: PPh3 / CH2Cl2 / 15 h / 20 °C
11.1: PCC; 4 Angstroem molecular sieves; AcONa / CH2Cl2 / 2 h / 0 °C
12.1: Dowex 50wX8 / tetrahydrofuran; H2O / 3 h / 20 °C
13.1: imidazole / dimethylformamide / 2 h / 0 °C
View Scheme
参考文献
Sato; Takimoto; Mori
Chemical and Pharmaceutical Bulletin, 2000 , vol. 48, # 11 p. 1753 - 1760
