[(8R,9S,13S,14S,17S)-3-乙酰氧基-13-甲基-6-氧代-8,9,11,12,14,15,16,17-八氢-7H-环戊二烯并[a]菲-17-基]乙酸酯合成路线 （共 12 条）
→
3434-45-5[(8R,9S,13S,14S,17S)-3-乙酰氧基-13-甲基-6-氧代-8,9,11,12,14,15,16,17-八氢-7H-环戊二烯并[a]菲-17-基]乙酸酯
反应条件
chromium(VI) oxide; acetic acid in ethyl acetate T=20°C; 28 h;
参考文献
Banerjee, Sharmila; Das, Tapas; Chakraborty, Sudipta; Samuel, Grace; Korde, Aruna; Venkatesh, Meera; Pillai
Bioorganic and Medicinal Chemistry, 2005 , vol. 13, # 13 p. 4315 - 4322
→
3434-45-5[(8R,9S,13S,14S,17S)-3-乙酰氧基-13-甲基-6-氧代-8,9,11,12,14,15,16,17-八氢-7H-环戊二烯并[a]菲-17-基]乙酸酯
反应条件
pyridine 3 h; Ambient temperature;
参考文献
Brevet, Jean-Luc; Fournet, Guy; Gore, Jacques
Synthetic Communications, 1996 , vol. 26, # 22 p. 4185 - 4193
→
3434-45-5[(8R,9S,13S,14S,17S)-3-乙酰氧基-13-甲基-6-氧代-8,9,11,12,14,15,16,17-八氢-7H-环戊二烯并[a]菲-17-基]乙酸酯
反应条件
1: 95 percent / pyridine, Ac2O / 8 h / 80 °C 2: 73 percent / CrO3, 3,5-dimethylpyrazole / CH2Cl2 / 0.33 h / -20 °C 3: 82 percent / CuBr / acetonitrile / 16 h / Ambient temperature 4: 100 percent / pyridine / 3 h / Ambient temperature View Scheme
参考文献
Brevet, Jean-Luc; Fournet, Guy; Gore, Jacques
Synthetic Communications, 1996 , vol. 26, # 22 p. 4185 - 4193
→
3434-45-5[(8R,9S,13S,14S,17S)-3-乙酰氧基-13-甲基-6-氧代-8,9,11,12,14,15,16,17-八氢-7H-环戊二烯并[a]菲-17-基]乙酸酯
反应条件
1: 73 percent / CrO3, 3,5-dimethylpyrazole / CH2Cl2 / 0.33 h / -20 °C 2: 82 percent / CuBr / acetonitrile / 16 h / Ambient temperature 3: 100 percent / pyridine / 3 h / Ambient temperature View Scheme
参考文献
Brevet, Jean-Luc; Fournet, Guy; Gore, Jacques
Synthetic Communications, 1996 , vol. 26, # 22 p. 4185 - 4193
→
3434-45-5[(8R,9S,13S,14S,17S)-3-乙酰氧基-13-甲基-6-氧代-8,9,11,12,14,15,16,17-八氢-7H-环戊二烯并[a]菲-17-基]乙酸酯
反应条件
1: 82 percent / CuBr / acetonitrile / 16 h / Ambient temperature 2: 100 percent / pyridine / 3 h / Ambient temperature View Scheme
参考文献
Brevet, Jean-Luc; Fournet, Guy; Gore, Jacques
Synthetic Communications, 1996 , vol. 26, # 22 p. 4185 - 4193
→
3434-45-5[(8R,9S,13S,14S,17S)-3-乙酰氧基-13-甲基-6-氧代-8,9,11,12,14,15,16,17-八氢-7H-环戊二烯并[a]菲-17-基]乙酸酯
反应条件
(i) CrO3, aq. H2SO4, acetone, (ii) /BRN= 385737/, NaOAc; Multistep reaction;
参考文献
Cambie,R.C. et al.
Tetrahedron, 1964 , vol. 20, p. 409 - 416
3434-45-5[(8R,9S,13S,14S,17S)-3-乙酰氧基-13-甲基-6-氧代-8,9,11,12,14,15,16,17-八氢-7H-环戊二烯并[a]菲-17-基]乙酸酯
→
反应条件
1: KOH / methanol 2: aq. NaOAc / methanol View Scheme
参考文献
Dean,P.D.G. et al.
Steroids, 1971 , vol. 18, p. 593 - 603
3434-45-5[(8R,9S,13S,14S,17S)-3-乙酰氧基-13-甲基-6-氧代-8,9,11,12,14,15,16,17-八氢-7H-环戊二烯并[a]菲-17-基]乙酸酯
→
反应条件
1: 92 percent / 20percent KOH / methanol / 24 h / Ambient temperature 2: 93 percent / CrO3, pyridine / acetone / 0.5 h / 0 °C 3: 1.) Li, NH2CH2CH2NH2 / 1.) 20 - 25 deg C, 2.) 20 - 25 deg C, 1,4-dioxane, 30 min View Scheme
参考文献
Weber, Gisela; Schaumann, J.; Carl, Constanze; Schwarz, S.; Leisner, Rosemarie
Journal fuer Praktische Chemie (Leipzig), 1989 , vol. 331, # 2 p. 223 - 230
3434-45-5[(8R,9S,13S,14S,17S)-3-乙酰氧基-13-甲基-6-氧代-8,9,11,12,14,15,16,17-八氢-7H-环戊二烯并[a]菲-17-基]乙酸酯
→
反应条件
1: ethanol / 4 h / Heating 2: 100 percent / ethanolic KOH 3: 70 percent / MeLi / dimethylformamide / 18.5 h / Ambient temperature View Scheme
参考文献
Ciattini, Pier Giuseppe; Morera, Enrico; Ortar, Giorgio
Synthetic Communications, 1990 , vol. 20, # 9 p. 1293 - 1297
3434-45-5[(8R,9S,13S,14S,17S)-3-乙酰氧基-13-甲基-6-氧代-8,9,11,12,14,15,16,17-八氢-7H-环戊二烯并[a]菲-17-基]乙酸酯
→
反应条件
potassium hydroxide in methanol 24 h; Ambient temperature;
参考文献
Weber, Gisela; Schaumann, J.; Carl, Constanze; Schwarz, S.; Leisner, Rosemarie
Journal fuer Praktische Chemie (Leipzig), 1989 , vol. 331, # 2 p. 223 - 230
