(-)-象牙(洪达木)酮宁合成路线 （共 78 条）
反应条件
1: 47 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Heating 2: 1) BF3*Et2O 2) PCC / 1) CH2Cl2, 0 deg C 2a) 9 h 2b) 4 h 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
N-chloro-succinimide; trifluoroacetic acid 1 h; Heating;
参考文献
Lewin, G.; Poisson, J.; Toffoli, P.
Tetrahedron, 1987 , vol. 43, # 3 p. 493 - 500
反应条件
1: 50 percent / toluene / 2 h / Ambient temperature 2: 50 percent / lithium iodide / dimethylformamide / 2 h / Heating 3: KOH, hydrogen peroxyde / methanol / 3 h / 80 °C 4: 49 percent / tetraethylammonium-tetrahydridoborate / CH2Cl2 / 0.5 h 5: CH2Cl2; methanol / 15 h / Ambient temperature 6: 96 percent / Huenig base / acetonitrile / 3 h / Heating 7: 1.) sodium hydride; 2.) lithium iodide / 1.) dioxan, ethanol, 15 min; 2.) dimethylformamide, reflux, 4.5 h 8: 70 percent / borontrifluorate etherate / CHCl3 / 17 h / Ambient temperature 9: 70 percent / Raney-Ni / acetone View Scheme
参考文献
Hakam, Khalida; Thielmann, Marion; Thielmann, Thomas; Winterfeldt, Ekkehard
Tetrahedron, 1987 , vol. 43, # 9 p. 2035 - 2044
反应条件
1: 70 percent / borontrifluorate etherate / CHCl3 / 17 h / Ambient temperature 2: 70 percent / Raney-Ni / acetone View Scheme
参考文献
Hakam, Khalida; Thielmann, Marion; Thielmann, Thomas; Winterfeldt, Ekkehard
Tetrahedron, 1987 , vol. 43, # 9 p. 2035 - 2044
反应条件
1: 1.) sodium hydride; 2.) lithium iodide / 1.) dioxan, ethanol, 15 min; 2.) dimethylformamide, reflux, 4.5 h 2: 70 percent / borontrifluorate etherate / CHCl3 / 17 h / Ambient temperature 3: 70 percent / Raney-Ni / acetone View Scheme
参考文献
Hakam, Khalida; Thielmann, Marion; Thielmann, Thomas; Winterfeldt, Ekkehard
Tetrahedron, 1987 , vol. 43, # 9 p. 2035 - 2044
反应条件
1: CH2Cl2; methanol / 15 h / Ambient temperature 2: 96 percent / Huenig base / acetonitrile / 3 h / Heating 3: 1.) sodium hydride; 2.) lithium iodide / 1.) dioxan, ethanol, 15 min; 2.) dimethylformamide, reflux, 4.5 h 4: 70 percent / borontrifluorate etherate / CHCl3 / 17 h / Ambient temperature 5: 70 percent / Raney-Ni / acetone View Scheme
参考文献
Hakam, Khalida; Thielmann, Marion; Thielmann, Thomas; Winterfeldt, Ekkehard
Tetrahedron, 1987 , vol. 43, # 9 p. 2035 - 2044
反应条件
1: 49 percent / tetraethylammonium-tetrahydridoborate / CH2Cl2 / 0.5 h 2: CH2Cl2; methanol / 15 h / Ambient temperature 3: 96 percent / Huenig base / acetonitrile / 3 h / Heating 4: 1.) sodium hydride; 2.) lithium iodide / 1.) dioxan, ethanol, 15 min; 2.) dimethylformamide, reflux, 4.5 h 5: 70 percent / borontrifluorate etherate / CHCl3 / 17 h / Ambient temperature 6: 70 percent / Raney-Ni / acetone View Scheme
参考文献
Hakam, Khalida; Thielmann, Marion; Thielmann, Thomas; Winterfeldt, Ekkehard
Tetrahedron, 1987 , vol. 43, # 9 p. 2035 - 2044
反应条件
1: 96 percent / Huenig base / acetonitrile / 3 h / Heating 2: 1.) sodium hydride; 2.) lithium iodide / 1.) dioxan, ethanol, 15 min; 2.) dimethylformamide, reflux, 4.5 h 3: 70 percent / borontrifluorate etherate / CHCl3 / 17 h / Ambient temperature 4: 70 percent / Raney-Ni / acetone View Scheme
参考文献
Hakam, Khalida; Thielmann, Marion; Thielmann, Thomas; Winterfeldt, Ekkehard
Tetrahedron, 1987 , vol. 43, # 9 p. 2035 - 2044
反应条件
1: KOH, hydrogen peroxyde / methanol / 3 h / 80 °C 2: 49 percent / tetraethylammonium-tetrahydridoborate / CH2Cl2 / 0.5 h 3: CH2Cl2; methanol / 15 h / Ambient temperature 4: 96 percent / Huenig base / acetonitrile / 3 h / Heating 5: 1.) sodium hydride; 2.) lithium iodide / 1.) dioxan, ethanol, 15 min; 2.) dimethylformamide, reflux, 4.5 h 6: 70 percent / borontrifluorate etherate / CHCl3 / 17 h / Ambient temperature 7: 70 percent / Raney-Ni / acetone View Scheme
参考文献
Hakam, Khalida; Thielmann, Marion; Thielmann, Thomas; Winterfeldt, Ekkehard
Tetrahedron, 1987 , vol. 43, # 9 p. 2035 - 2044
反应条件
1: 50 percent / lithium iodide / dimethylformamide / 2 h / Heating 2: KOH, hydrogen peroxyde / methanol / 3 h / 80 °C 3: 49 percent / tetraethylammonium-tetrahydridoborate / CH2Cl2 / 0.5 h 4: CH2Cl2; methanol / 15 h / Ambient temperature 5: 96 percent / Huenig base / acetonitrile / 3 h / Heating 6: 1.) sodium hydride; 2.) lithium iodide / 1.) dioxan, ethanol, 15 min; 2.) dimethylformamide, reflux, 4.5 h 7: 70 percent / borontrifluorate etherate / CHCl3 / 17 h / Ambient temperature 8: 70 percent / Raney-Ni / acetone View Scheme
参考文献
Hakam, Khalida; Thielmann, Marion; Thielmann, Thomas; Winterfeldt, Ekkehard
Tetrahedron, 1987 , vol. 43, # 9 p. 2035 - 2044
