(1S,4R)-顺式-4-乙酰氧基-2-环戊烯-1-醇合成路线 （共 38 条）
反应条件
sodium hydride; triphenylphosphine; tetrakis(triphenylphosphine) palladium(0)
参考文献
Weigl, Ulrich; Heimberger, Martin; Pierik, Antonio J.; Retey, Janos
Chemistry - A European Journal, 2003 , vol. 9, # 3 p. 652 - 660
反应条件
1: 94 percent / N-methylmorpholine N-oxide (NMO), OsO4 / acetone; H2O
2: 79 percent / p-toluenesulfonic acid (p-TSA) / acetone / Ambient temperature
3: 80 percent / pyridinium chlorochromate, diatomaceous earth / CH2Cl2 / 48 h / Ambient temperature
View Scheme
参考文献
Deardorff, Donald R.; Shambayati, Soroosh; Myles, David C.; Heerding, Dirk
Journal of Organic Chemistry, 1988 , vol. 53, # 15 p. 3614 - 3615
反应条件
Yield given. Multistep reaction;
参考文献
Dols; Klunder; Zwanenburg
Tetrahedron, 1994 , vol. 50, # 28 p. 8515 - 8538
反应条件
1: 68 percent / 1,1'-bis(diphenylphosphino)ferrocene; tris(dibenzylideneacetone)dipalladium; N,O-bis(trimethylsilyl)acetamide / tetrahydrofuran / 3 h / 45 °C
2: 96 percent / trifluoroacetic acid / CH2Cl2 / 20 h
View Scheme
参考文献
Dauvergne, Jerome; Happe, Alan M.; Jadhav, Vasudev; Justice, David; Matos, Marie-Christine; McCormack, Peter J.; Pitts, Michael R.; Roberts, Stanley M.; Singh, Sanjay K.; Snape, Timothy J.; Whittall, John
Tetrahedron, 2004 , vol. 60, # 11 p. 2559 - 2567
反应条件
1.1: 100 percent / imidazole / tetrahydrofuran / 24 h / 20 °C
2.1: 90 percent / NaOMe; MeOH / 24 h / 20 °C
3.1: DMAP / dimethylformamide / 20 h / 100 °C
4.1: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C
5.1: 84 percent / diisopropylethylamine; methanesulfonyl chloride / CH2Cl2 / 3 h / 0 °C
6.1: NaH / tetrahydrofuran / 0 - 20 °C
6.2: 72 percent / tetrahydrofuran / 19 h / 75 °C
7.1: 80 percent / LiI / dimethylformamide / 17 h / 130 °C
8.1: 39 percent / p-toluenesulfonic acid / methanol / 1.25 h / 20 °C
View Scheme
参考文献
Levy, Daniel E.; Bao, Ming; Cherbavaz James, Diana B.; Tomlinson; Sedlock, David M.; Homcy, Charles J.; Scarborough, Robert M.
Journal of Medicinal Chemistry, 2003 , vol. 46, # 11 p. 2177 - 2186
反应条件
1.1: 100 percent / imidazole / tetrahydrofuran / 24 h / 20 °C
2.1: 90 percent / NaOMe; MeOH / 24 h / 20 °C
3.1: 81 percent / triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 18 h / 20 - 40 °C
4.1: 85 percent / NaOMe; MeOH / 24 h / 20 °C
5.1: 99 percent / diisopropylethylamine; methanesulfonyl chloride / CH2Cl2 / 3 h / 0 °C
6.1: NaH / tetrahydrofuran / 0 - 20 °C
6.2: 75 percent / tetrahydrofuran / 19 h / 75 °C
7.1: 74 percent / LiI / dimethylformamide / 17 h / 130 °C
8.1: 59 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C
View Scheme
参考文献
Levy, Daniel E.; Bao, Ming; Cherbavaz James, Diana B.; Tomlinson; Sedlock, David M.; Homcy, Charles J.; Scarborough, Robert M.
Journal of Medicinal Chemistry, 2003 , vol. 46, # 11 p. 2177 - 2186
反应条件
1.1: 100 percent / imidazole / tetrahydrofuran / 24 h / 20 °C
2.1: 90 percent / NaOMe; MeOH / 24 h / 20 °C
3.1: DMAP / dimethylformamide / 20 h / 100 °C
4.1: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C
5.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 18 h / 20 - 40 °C
6.1: NaOMe; MeOH / 24 h / 20 °C
7.1: 93 percent / diisopropylethylamine; methanesulfonyl chloride / CH2Cl2 / 3 h / 0 °C
8.1: NaH / tetrahydrofuran / 0 - 20 °C
8.2: 74 percent / tetrahydrofuran / 19 h / 75 °C
9.1: 63 percent / LiI / dimethylformamide / 17 h / 130 °C
10.1: 54 percent / p-toluenesulfonic acid / methanol / 1.25 h / 20 °C
View Scheme
参考文献
Levy, Daniel E.; Bao, Ming; Cherbavaz James, Diana B.; Tomlinson; Sedlock, David M.; Homcy, Charles J.; Scarborough, Robert M.
Journal of Medicinal Chemistry, 2003 , vol. 46, # 11 p. 2177 - 2186
反应条件
trifluoroacetic acid in dichloromethane
参考文献
Marion Merrell Dow Inc.
Patent: US5244896 A1, 1993 ;
