Defucogilvocarcin V合成路线 （共 43 条）
反应条件
1: 55 percent / diisopropylethylamine / CH2Cl2 / 4 h / Ambient temperature
2: diisopropylethylamine / CH2Cl2 / 8 h
3: 37 percent / 40percent aq. NaOH / dioxane / 9 h / Ambient temperature
4: 1.) n-BuLi, 2.) MgBr / 1.) hexane, THF, -78 deg C, 5 min, 2.) ether, benzene, from -78 deg C to RT, 1.5 h
5: 86 percent / aq. HCl / tetrahydrofuran / 2 h / Heating
View Scheme
参考文献
Patten; Nguyen; Danishefsky
Journal of Organic Chemistry, 1988 , vol. 53, # 5 p. 1003 - 1007
反应条件
1: CH2Cl2 / 5 h / 0 - 20 °C
2: thionyl chloride / CH2Cl2 / 2 h / 0 °C
3: 1.) n-BuLi, 2.) MgBr / 1.) hexane, THF, -78 deg C, 5 min, 2.) ether, benzene, from -78 deg C to RT, 1.5 h
4: 86 percent / aq. HCl / tetrahydrofuran / 2 h / Heating
View Scheme
参考文献
Patten; Nguyen; Danishefsky
Journal of Organic Chemistry, 1988 , vol. 53, # 5 p. 1003 - 1007
反应条件
1: diisopropylethylamine / CH2Cl2 / 8 h
2: 37 percent / 40percent aq. NaOH / dioxane / 9 h / Ambient temperature
3: 1.) n-BuLi, 2.) MgBr / 1.) hexane, THF, -78 deg C, 5 min, 2.) ether, benzene, from -78 deg C to RT, 1.5 h
4: 86 percent / aq. HCl / tetrahydrofuran / 2 h / Heating
View Scheme
参考文献
Patten; Nguyen; Danishefsky
Journal of Organic Chemistry, 1988 , vol. 53, # 5 p. 1003 - 1007
反应条件
1: 1.) n-BuLi, 2.) MgBr / 1.) hexane, THF, -78 deg C, 5 min, 2.) ether, benzene, from -78 deg C to RT, 1.5 h
2: 86 percent / aq. HCl / tetrahydrofuran / 2 h / Heating
View Scheme
参考文献
Patten; Nguyen; Danishefsky
Journal of Organic Chemistry, 1988 , vol. 53, # 5 p. 1003 - 1007
反应条件
1: 37 percent / 40percent aq. NaOH / dioxane / 9 h / Ambient temperature
2: 1.) n-BuLi, 2.) MgBr / 1.) hexane, THF, -78 deg C, 5 min, 2.) ether, benzene, from -78 deg C to RT, 1.5 h
3: 86 percent / aq. HCl / tetrahydrofuran / 2 h / Heating
View Scheme
参考文献
Patten; Nguyen; Danishefsky
Journal of Organic Chemistry, 1988 , vol. 53, # 5 p. 1003 - 1007
反应条件
1: 1.) n-BuLi, 2.) MgBr / 1.) hexane, THF, -78 deg C, 5 min, 2.) ether, benzene, from -78 deg C to RT, 1.5 h
2: 86 percent / aq. HCl / tetrahydrofuran / 2 h / Heating
View Scheme
参考文献
Patten; Nguyen; Danishefsky
Journal of Organic Chemistry, 1988 , vol. 53, # 5 p. 1003 - 1007
反应条件
1: 65 percent / pyridine / 12 h
2: 48 mg / N-bromosuccinimide (NBS), benzoyl peroxide / CCl4 / 0.33 h / Heating
3: 34 mg / LiBr, Li2CO3, hydroquinone / dimethylformamide / 110 °C
4: sodium methoxide / methanol
View Scheme
参考文献
McGee, Lawrence R.; Confalone, Pat N.
Journal of Organic Chemistry, 1988 , vol. 53, # 16 p. 3695 - 3701
反应条件
1: CH2Cl2 / Ambient temperature
2: 81 percent / tetrahydrofuran / 15 h / Ambient temperature
3: 1.) hydriodic acid; 2.) hydriodic acid / 1.) glacial acetic acid, reflux, 2 h; 2.) acetic acid, reflux, 7 h
4: 1.) potassium carbonate; 2.) pyridine, dimethylaminopyridine / 1.) DMSO, acetone, r.t., 2 h
5: 75 percent / N-bromosuccinimide, dibenzoylperoxide / CCl4 / 6 h / Heating
6: 1.) sodium borohydride, diphenyl diselenide; 2.) 30percent H2O2 / 1.) ethanol, THF, 2.5 h, reflux; 2.) THF, ethanol, 3 h, 0 deg C
View Scheme
参考文献
Findlay, John A.; Daljeet, Anand; Murray, Peter John; Rej, Rabindra N.
Canadian Journal of Chemistry, 1987 , vol. 65, p. 427 - 431
反应条件
1: 4.6 g / thionyl chloride / 8 h / Heating
2: CH2Cl2 / Ambient temperature
3: 81 percent / tetrahydrofuran / 15 h / Ambient temperature
4: 1.) hydriodic acid; 2.) hydriodic acid / 1.) glacial acetic acid, reflux, 2 h; 2.) acetic acid, reflux, 7 h
5: 1.) potassium carbonate; 2.) pyridine, dimethylaminopyridine / 1.) DMSO, acetone, r.t., 2 h
6: 75 percent / N-bromosuccinimide, dibenzoylperoxide / CCl4 / 6 h / Heating
7: 1.) sodium borohydride, diphenyl diselenide; 2.) 30percent H2O2 / 1.) ethanol, THF, 2.5 h, reflux; 2.) THF, ethanol, 3 h, 0 deg C
View Scheme
参考文献
Findlay, John A.; Daljeet, Anand; Murray, Peter John; Rej, Rabindra N.
Canadian Journal of Chemistry, 1987 , vol. 65, p. 427 - 431
反应条件
1: 81 percent / tetrahydrofuran / 15 h / Ambient temperature
2: 1.) hydriodic acid; 2.) hydriodic acid / 1.) glacial acetic acid, reflux, 2 h; 2.) acetic acid, reflux, 7 h
3: 1.) potassium carbonate; 2.) pyridine, dimethylaminopyridine / 1.) DMSO, acetone, r.t., 2 h
4: 75 percent / N-bromosuccinimide, dibenzoylperoxide / CCl4 / 6 h / Heating
5: 1.) sodium borohydride, diphenyl diselenide; 2.) 30percent H2O2 / 1.) ethanol, THF, 2.5 h, reflux; 2.) THF, ethanol, 3 h, 0 deg C
View Scheme
参考文献
Findlay, John A.; Daljeet, Anand; Murray, Peter John; Rej, Rabindra N.
Canadian Journal of Chemistry, 1987 , vol. 65, p. 427 - 431
