(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 合成路线 （共 38 条）
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反应条件
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: 94 percent / tributylamine, 98percent formic acid / Pd(OAc)2(Ph3P)2 / dimethylformamide / 0.5 h / 70 °C
2: K2CO3 / CH2Cl2; methanol / 0.08 h / 25 °C
3: bis<α,α-bis(trifluoromethyl)benzenemethanolato>diphenylsulfur / CH2Cl2 / 0.25 h / 0 °C
4: 96 percent / NaOMe / toluene; methanol / 12 h / 25 °C
View Scheme
参考文献
Dolle; Schmidt; Erhard; Kruse
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反应条件
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
sulfuric acid in 1,4-dioxane
70 h; Heating;
参考文献
Blume, Thorsten; Guttzeit, Marc; Kuhnke, Joachim; Zorn, Ludwig
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反应条件
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
lithium aluminium tetrahydride in tetrahydrofuran
Reduction;
参考文献
Murray, Anthony; Gronvald, Frederik C.; Nielsen, Jane K.; Faarup, Peter
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反应条件
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: K2CO3 / CH2Cl2; methanol / 0.08 h / 25 °C
2: bis<α,α-bis(trifluoromethyl)benzenemethanolato>diphenylsulfur / CH2Cl2 / 0.25 h / 0 °C
3: 96 percent / NaOMe / toluene; methanol / 12 h / 25 °C
View Scheme
参考文献
Dolle; Schmidt; Erhard; Kruse
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反应条件
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
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反应条件
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: 68 percent / t-BuOK / 2-methyl-propan-2-ol / 0.5 h / 20 °C
2: 79 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 20 °C
3: 69 percent / H2SO4 / dioxane / 70 h / Heating
View Scheme
参考文献
Blume, Thorsten; Guttzeit, Marc; Kuhnke, Joachim; Zorn, Ludwig
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反应条件
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: 79 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 20 °C
2: 69 percent / H2SO4 / dioxane / 70 h / Heating
View Scheme
参考文献
Blume, Thorsten; Guttzeit, Marc; Kuhnke, Joachim; Zorn, Ludwig
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反应条件
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: 72 percent / pyridine; 4-(dimethylamino)pyridine / 2 h / 50 °C
2: 100 percent / Li2CuCl3 / tetrahydrofuran / -30 - 20 °C
3: 69 percent / H2SO4 / dioxane / 70 h / Heating
View Scheme
参考文献
Blume, Thorsten; Guttzeit, Marc; Kuhnke, Joachim; Zorn, Ludwig
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反应条件
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: t-BuOK / 2-methyl-propan-2-ol / 0.5 h / 20 °C
2: LiAlH4 / tetrahydrofuran / 0.5 h / 20 °C
3: pyridine / 1 h / 0 °C
4: 1,3-dibromo-5,5-dimethyl-imidazolidine-2,4-dione / benzene; hexane / 0.5 h / 70 °C
5: 2,4,6-trimethylpyridine / toluene / 2 h / Heating
6: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C
7: 72 percent / pyridine; 4-(dimethylamino)pyridine / 2 h / 50 °C
8: 100 percent / Li2CuCl3 / tetrahydrofuran / -30 - 20 °C
9: 69 percent / H2SO4 / dioxane / 70 h / Heating
View Scheme
参考文献
Blume, Thorsten; Guttzeit, Marc; Kuhnke, Joachim; Zorn, Ludwig
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反应条件
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: LiAlH4 / tetrahydrofuran / 0.5 h / 20 °C
2: pyridine / 1 h / 0 °C
3: 1,3-dibromo-5,5-dimethyl-imidazolidine-2,4-dione / benzene; hexane / 0.5 h / 70 °C
4: 2,4,6-trimethylpyridine / toluene / 2 h / Heating
5: tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C
6: 72 percent / pyridine; 4-(dimethylamino)pyridine / 2 h / 50 °C
7: 100 percent / Li2CuCl3 / tetrahydrofuran / -30 - 20 °C
8: 69 percent / H2SO4 / dioxane / 70 h / Heating
View Scheme
参考文献
Blume, Thorsten; Guttzeit, Marc; Kuhnke, Joachim; Zorn, Ludwig
