(20S)-21-羟基-20-甲基孕甾-4-烯-3-酮合成路线 （共 5 条）
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1715-86-2(3S,9R,10R,13S,14R,17R)-10,13-二甲基-17-[(2R)-6-甲基庚-5-烯-2-基]-2,3,4,9,11,12,14,15,16,17-十氢-1H-环戊并[a]菲-3-醇
反应条件
1: 51 percent / triphenylphosphane, CCl4 / 48 h / Heating 2: 88 percent / p-toluenesulfonic acid / 1 h / 80 - 90 °C 3: 90 percent / NaBH4/H2O / tetrahydrofuran; 2-methoxy-ethanol / 24 h / Ambient temperature 4: 88 percent / pyridine / 12 h / Ambient temperature 5: N-bromosuccinimide, dibenzoylperoxide / CCl4 / 0.17 h / 80 °C / Irradiation 6: 1) trimethylphosphite / 1) 90 min, 125 deg C, xylol; 2) CH2Cl2 7: 95 percent / Na / methanol / 2 h / Heating 8: 90 percent / imidazole / dimethylformamide / 12 h / Ambient temperature 9: 69 percent / NaHCO3 / dimethylsulfoxide / 0.25 h / 150 °C 10: 71 percent / THF / acetone / Heating 11: 91 percent / Na / methanol / 2 h / Heating 12: 71 percent / pyridine / 12 h / 0 °C 13: 66 percent / NaHCO3 / dimethylsulfoxide / 0.25 h / 150 °C 14: 73 percent / tetrahydrofuran / 12 h / Ambient temperature 15: 81 percent / 40 percent HF / acetonitrile / 1 h / Ambient temperature 16: 44 percent / imidazole / dimethylformamide / 12 h / Ambient temperature 17: 44 percent / tetrahydrofuran / 12 h / Ambient temperature 18: 61 percent / 40 percent HF / acetonitrile / 1 h / Ambient temperature 19: 32 percent / molecular sieve (4 Angstroem) / tetrahydrofuran / 14 h / Ambient temperature View Scheme
参考文献
, vol. No. 6, p. 1031 - 1042
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64284-64-6(3R,5S,10S,13S,17S)-4,4,10,13-四甲基-17-[(2R)-6-甲基庚-5-烯-2-基]-1,2,3,5,6,7,11,12,16,17-十氢环戊烯并[a]菲-3-醇
反应条件
1: imidazole / CH2Cl2 / 4 h / 20 °C
2: t-BuOK / 2-methyl-propan-2-ol / 0.5 h / 20 °C
3: LiAlH4 / tetrahydrofuran / 0.5 h / 20 °C
4: pyridine / 1 h / 0 °C
5: 1,3-dibromo-5,5-dimethyl-imidazolidine-2,4-dione / benzene; hexane / 0.5 h / 70 °C
6: 2,4,6-trimethylpyridine / toluene / 2 h / Heating
7: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C
8: 72 percent / pyridine; 4-(dimethylamino)pyridine / 2 h / 50 °C
9: 100 percent / Li2CuCl3 / tetrahydrofuran / -30 - 20 °C
10: 69 percent / H2SO4 / dioxane / 70 h / Heating
View Scheme
参考文献
Blume, Thorsten; Guttzeit, Marc; Kuhnke, Joachim; Zorn, Ludwig
Organic Letters, 2003 , vol. 5, # 11 p. 1837 - 1839
反应条件
Multi-step reaction with 4 steps 1: imidazole / CH2Cl2 / 4 h / 20 °C2: t-BuOK / 2-methyl-propan-2-ol / 0.5 h / 20 °C3: LiAlH4 / tetrahydrofuran / 0.5 h / 20 °C4: pyridine / 1 h / 0 °C
参考文献
Blume, Thorsten; Guttzeit, Marc; Kuhnke, Joachim; Zorn, Ludwig Organic Letters, 2003 , vol. 5, # 11 p. 1837 - 1839
反应条件
Multi-step reaction with 9 steps 1: imidazole / CH2Cl2 / 4 h / 20 °C2: t-BuOK / 2-methyl-propan-2-ol / 0.5 h / 20 °C3: LiAlH4 / tetrahydrofuran / 0.5 h / 20 °C4: pyridine / 1 h / 0 °C5: 1,3-dibromo-5,5-dimethyl-imidazolidine-2,4-dione / benzene; hexane / 0.5 h / 70 °C6: 2,4,6-trimethylpyridine / toluene / 2 h / Heating7: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C8: 72 percent / pyridine; 4-(dimethylamino)pyridine / 2 h / 50 °C9: 100 percent / Li2CuCl3 / tetrahydrofuran / -30 - 20 °C
参考文献
Blume, Thorsten; Guttzeit, Marc; Kuhnke, Joachim; Zorn, Ludwig Organic Letters, 2003 , vol. 5, # 11 p. 1837 - 1839
反应条件
Multi-step reaction with 7 steps 1: imidazole / CH2Cl2 / 4 h / 20 °C2: t-BuOK / 2-methyl-propan-2-ol / 0.5 h / 20 °C3: LiAlH4 / tetrahydrofuran / 0.5 h / 20 °C4: pyridine / 1 h / 0 °C5: 1,3-dibromo-5,5-dimethyl-imidazolidine-2,4-dione / benzene; hexane / 0.5 h / 70 °C6: 2,4,6-trimethylpyridine / toluene / 2 h / Heating7: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C
参考文献
Blume, Thorsten; Guttzeit, Marc; Kuhnke, Joachim; Zorn, Ludwig Organic Letters, 2003 , vol. 5, # 11 p. 1837 - 1839
