(-)-象牙(洪达木)酮宁合成路线 （共 78 条）
反应条件
1: 88 percent / CF3CO2H / CH2Cl2 / 10 h / -55 °C 2: 1.) BH3, 2.) 6 N NaOH, H2O2 / 1.) THF, room temperature, 2 h, 2.) EtOH, H2O, 55 deg C, 1.5 h 3: 97 percent / molecular sieves, NMO, TPAP / CH2Cl2 / 1 h View Scheme
参考文献
Schultz, Arthur G.; Pettus, Liping
Journal of Organic Chemistry, 1997 , vol. 62, # 20 p. 6855 - 6861
反应条件
1: 70 percent / molecular sieves, NMO, TPAP / CH2Cl2 / 2 h / Ambient temperature 2: 88 percent / CF3CO2H / CH2Cl2 / 10 h / -55 °C 3: 1.) BH3, 2.) 6 N NaOH, H2O2 / 1.) THF, room temperature, 2 h, 2.) EtOH, H2O, 55 deg C, 1.5 h 4: 97 percent / molecular sieves, NMO, TPAP / CH2Cl2 / 1 h View Scheme
参考文献
Schultz, Arthur G.; Pettus, Liping
Journal of Organic Chemistry, 1997 , vol. 62, # 20 p. 6855 - 6861
反应条件
1: 1.) BH3, 2.) 6 N NaOH, H2O2 / 1.) THF, room temperature, 2 h, 2.) EtOH, H2O, 55 deg C, 1.5 h 2: 97 percent / molecular sieves, NMO, TPAP / CH2Cl2 / 1 h View Scheme
参考文献
Schultz, Arthur G.; Pettus, Liping
Journal of Organic Chemistry, 1997 , vol. 62, # 20 p. 6855 - 6861
反应条件
1: 84 percent / KH / tetrahydrofuran / 3 h / Ambient temperature 2: 70 percent / molecular sieves, NMO, TPAP / CH2Cl2 / 2 h / Ambient temperature 3: 88 percent / CF3CO2H / CH2Cl2 / 10 h / -55 °C 4: 1.) BH3, 2.) 6 N NaOH, H2O2 / 1.) THF, room temperature, 2 h, 2.) EtOH, H2O, 55 deg C, 1.5 h 5: 97 percent / molecular sieves, NMO, TPAP / CH2Cl2 / 1 h View Scheme
参考文献
Schultz, Arthur G.; Pettus, Liping
Journal of Organic Chemistry, 1997 , vol. 62, # 20 p. 6855 - 6861
反应条件
1: 84 percent / LiBH4 / methanol; tetrahydrofuran / 48 h / Ambient temperature 2: 84 percent / KH / tetrahydrofuran / 3 h / Ambient temperature 3: 70 percent / molecular sieves, NMO, TPAP / CH2Cl2 / 2 h / Ambient temperature 4: 88 percent / CF3CO2H / CH2Cl2 / 10 h / -55 °C 5: 1.) BH3, 2.) 6 N NaOH, H2O2 / 1.) THF, room temperature, 2 h, 2.) EtOH, H2O, 55 deg C, 1.5 h 6: 97 percent / molecular sieves, NMO, TPAP / CH2Cl2 / 1 h View Scheme
参考文献
Schultz, Arthur G.; Pettus, Liping
Journal of Organic Chemistry, 1997 , vol. 62, # 20 p. 6855 - 6861
反应条件
1: 81 percent / m-CPBA / CH2Cl2 / 36 h 2: TsOH*H2O / benzene; H2O / 24 h / Heating 3: 71 percent / Et3N, (PhO)2P(O)N3 / tetrahydrofuran / Ambient temperature 4: 84 percent / LiBH4 / methanol; tetrahydrofuran / 48 h / Ambient temperature 5: 84 percent / KH / tetrahydrofuran / 3 h / Ambient temperature 6: 70 percent / molecular sieves, NMO, TPAP / CH2Cl2 / 2 h / Ambient temperature 7: 88 percent / CF3CO2H / CH2Cl2 / 10 h / -55 °C 8: 1.) BH3, 2.) 6 N NaOH, H2O2 / 1.) THF, room temperature, 2 h, 2.) EtOH, H2O, 55 deg C, 1.5 h 9: 97 percent / molecular sieves, NMO, TPAP / CH2Cl2 / 1 h View Scheme
参考文献
Schultz, Arthur G.; Pettus, Liping
Journal of Organic Chemistry, 1997 , vol. 62, # 20 p. 6855 - 6861
反应条件
1: TsOH*H2O / benzene; H2O / 24 h / Heating 2: 71 percent / Et3N, (PhO)2P(O)N3 / tetrahydrofuran / Ambient temperature 3: 84 percent / LiBH4 / methanol; tetrahydrofuran / 48 h / Ambient temperature 4: 84 percent / KH / tetrahydrofuran / 3 h / Ambient temperature 5: 70 percent / molecular sieves, NMO, TPAP / CH2Cl2 / 2 h / Ambient temperature 6: 88 percent / CF3CO2H / CH2Cl2 / 10 h / -55 °C 7: 1.) BH3, 2.) 6 N NaOH, H2O2 / 1.) THF, room temperature, 2 h, 2.) EtOH, H2O, 55 deg C, 1.5 h 8: 97 percent / molecular sieves, NMO, TPAP / CH2Cl2 / 1 h View Scheme
参考文献
Schultz, Arthur G.; Pettus, Liping
Journal of Organic Chemistry, 1997 , vol. 62, # 20 p. 6855 - 6861
反应条件
1: 391 mg / Jones reagent / acetone; propan-2-ol; H2O / 0 °C 2: 1 percent / DIBAH / diethyl ether / -78 °C 3: p-TsOH / diethyl ether / 40 h / Heating 4: 2) 20percent NaOH / 1) HOAc, reflux, 6 d 2) MeOH, r.t., 30 min 5: 53 percent / CrO3, pyridine / 2 h / Ambient temperature 6: 1) LiAlH4 2) CrO3, pyridine / 1) ether, reflux, 2 h 2) r.t., 30 min View Scheme
参考文献
Node, Manabu; Nagasawa, Hideko; Fuji, Kaoru
Journal of Organic Chemistry, 1990 , vol. 55, # 2 p. 517 - 521
反应条件
1: 1 percent / DIBAH / diethyl ether / -78 °C 2: p-TsOH / diethyl ether / 40 h / Heating 3: 2) 20percent NaOH / 1) HOAc, reflux, 6 d 2) MeOH, r.t., 30 min 4: 53 percent / CrO3, pyridine / 2 h / Ambient temperature 5: 1) LiAlH4 2) CrO3, pyridine / 1) ether, reflux, 2 h 2) r.t., 30 min View Scheme
参考文献
Node, Manabu; Nagasawa, Hideko; Fuji, Kaoru
Journal of Organic Chemistry, 1990 , vol. 55, # 2 p. 517 - 521
反应条件
1: TiCl3, NH4OAc / 1,2-dimethoxy-ethane; H2O / 10 h / Ambient temperature 2: 1) NaBH4 2) 9percent HCl / 1) MeOH, r.t., 40 min 2) reflux, 1h 3: 391 mg / Jones reagent / acetone; propan-2-ol; H2O / 0 °C 4: 1 percent / DIBAH / diethyl ether / -78 °C 5: p-TsOH / diethyl ether / 40 h / Heating 6: 2) 20percent NaOH / 1) HOAc, reflux, 6 d 2) MeOH, r.t., 30 min 7: 53 percent / CrO3, pyridine / 2 h / Ambient temperature 8: 1) LiAlH4 2) CrO3, pyridine / 1) ether, reflux, 2 h 2) r.t., 30 min View Scheme
参考文献
Node, Manabu; Nagasawa, Hideko; Fuji, Kaoru
Journal of Organic Chemistry, 1990 , vol. 55, # 2 p. 517 - 521
