(-)-象牙(洪达木)酮宁合成路线 （共 78 条）
反应条件
N-methyl-2-indolinone; molecular sieve; tetrapropylammonium perruthennate in dichloromethane 1 h;
参考文献
Schultz, Arthur G.; Pettus, Liping
Journal of Organic Chemistry, 1997 , vol. 62, # 20 p. 6855 - 6861
反应条件
sodium hydroxide in water; ethylene glycol T=160°C; 3 h;
参考文献
Nemes, Andras; Czibula, Laszlo; Visky, Gyorgy; Farkas, Maria; Kreidl, Janos
Heterocycles, 1991 , vol. 32, # 12 p. 2329 - 2338
反应条件
1: 30 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Heating 2: Py*SO3; Et3N / dimethylsulfoxide / 20 h / 20 °C 3: 2 mg / NMMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 3 h / 20 °C View Scheme
参考文献
Node; Nagasawa; Fuji
Journal of the American Chemical Society, 1987 , vol. 109, # 25 p. 7901 - 7903
反应条件
sodium tetrahydroborate; boron trifluoride diethyl etherate; dihydrogen peroxide; sodium hydroxide in tetrahydrofuran T=0 - 40°C;
参考文献
Woods, James R.; Riofski, Mark V.; Zheng, Mary M.; O'Banion, Melissa A.; Mo, Huaping; Kirshner, Julia; Colby, David A.
Bioorganic and Medicinal Chemistry Letters, 2013 , vol. 23, # 21 p. 5865 - 5869
反应条件
1.1: 25 percent / LiAlH4 / -78 °C 2.1: 86 percent / DCC; DMAP / CH2Cl2 / 1 h / 0 °C 3.1: disiamylborane / tetrahydrofuran / 0 - 20 °C 3.2: 74 percent / H2O2; NaOH / tetrahydrofuran; H2O / 0.33 h / 10 - 20 °C 4.1: 89 percent / pyridine / 12 h / 0 - 20 °C 5.1: 88 percent / MsN3; Et3N / acetonitrile / 10 h / 20 °C 6.1: 87 percent / Rh2(OAc)4 / CH2Cl2 / 14 h / Heating 7.1: 84 percent / NaCl; H2O / dimethylsulfoxide / 12 h / 110 °C 8.1: 93 percent / Bu4NF / tetrahydrofuran / 0.67 h / 20 °C 9.1: 98 percent / Jones reagent / acetone / 0 °C 10.1: DCC / CH2Cl2 / 1 h / 0 °C 10.2: 67 percent / CH2Cl2 / 15 h / 20 °C 11.1: 92 percent / LiBH4 / tetrahydrofuran; methanol / 48 h / 20 °C 12.1: 92 percent / imidazole / dimethylformamide / 16 h / -20 - 20 °C 13.1: Et3N; Py*SO3 / dimethylsulfoxide / 60 h / 20 °C 13.2: 18.7 mg / TFA / CH2Cl2 / 16 h / -42 - 20 °C 14.1: 96 percent / Me3SiCl / methanol / 3 h / 0 - 20 °C 15.1: 30 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Heating 16.1: Py*SO3; Et3N / dimethylsulfoxide / 20 h / 20 °C 17.1: 2 mg / NMMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 3 h / 20 °C View Scheme
参考文献
Wee; Yu
Journal of Organic Chemistry, 2001 , vol. 66, # 26 p. 8935 - 8943
反应条件
1.1: 87 percent / Rh2(OAc)4 / CH2Cl2 / 14 h / Heating 2.1: 84 percent / NaCl; H2O / dimethylsulfoxide / 12 h / 110 °C 3.1: 93 percent / Bu4NF / tetrahydrofuran / 0.67 h / 20 °C 4.1: 98 percent / Jones reagent / acetone / 0 °C 5.1: DCC / CH2Cl2 / 1 h / 0 °C 5.2: 67 percent / CH2Cl2 / 15 h / 20 °C 6.1: 92 percent / LiBH4 / tetrahydrofuran; methanol / 48 h / 20 °C 7.1: 92 percent / imidazole / dimethylformamide / 16 h / -20 - 20 °C 8.1: Et3N; Py*SO3 / dimethylsulfoxide / 60 h / 20 °C 8.2: 18.7 mg / TFA / CH2Cl2 / 16 h / -42 - 20 °C 9.1: 96 percent / Me3SiCl / methanol / 3 h / 0 - 20 °C 10.1: 30 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Heating 11.1: Py*SO3; Et3N / dimethylsulfoxide / 20 h / 20 °C 12.1: 2 mg / NMMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 3 h / 20 °C View Scheme
参考文献
Wee, Andrew G.H.; Yu, Qing
Tetrahedron Letters, 2000 , vol. 41, # 5 p. 587 - 590
反应条件
1.1: 92 percent / DMAP; pyridine / CH2Cl2 / 3 h / 20 °C 2.1: 76 percent / Bu3SnH; AIBN / toluene / 12 h / 75 °C 3.1: 100 percent / LiOH*H2O; H2O2 / tetrahydrofuran; H2O / 1 h / 0 °C 4.1: 0.023 g / LiAlH4 / diethyl ether / 0 - 20 °C 5.1: 86 percent / DCC; DMAP / CH2Cl2 / 1 h / 0 °C 6.1: disiamylborane / tetrahydrofuran / 0 - 20 °C 6.2: 74 percent / H2O2; NaOH / tetrahydrofuran; H2O / 0.33 h / 10 - 20 °C 7.1: 89 percent / pyridine / 12 h / 0 - 20 °C 8.1: 88 percent / MsN3; Et3N / acetonitrile / 10 h / 20 °C 9.1: 87 percent / Rh2(OAc)4 / CH2Cl2 / 14 h / Heating 10.1: 84 percent / NaCl; H2O / dimethylsulfoxide / 12 h / 110 °C 11.1: 93 percent / Bu4NF / tetrahydrofuran / 0.67 h / 20 °C 12.1: 98 percent / Jones reagent / acetone / 0 °C 13.1: DCC / CH2Cl2 / 1 h / 0 °C 13.2: 67 percent / CH2Cl2 / 15 h / 20 °C 14.1: 92 percent / LiBH4 / tetrahydrofuran; methanol / 48 h / 20 °C 15.1: 92 percent / imidazole / dimethylformamide / 16 h / -20 - 20 °C 16.1: Et3N; Py*SO3 / dimethylsulfoxide / 60 h / 20 °C 16.2: 18.7 mg / TFA / CH2Cl2 / 16 h / -42 - 20 °C 17.1: 96 percent / Me3SiCl / methanol / 3 h / 0 - 20 °C 18.1: 30 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Heating 19.1: Py*SO3; Et3N / dimethylsulfoxide / 20 h / 20 °C 20.1: 2 mg / NMMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 3 h / 20 °C View Scheme
参考文献
Wee; Yu
Journal of Organic Chemistry, 2001 , vol. 66, # 26 p. 8935 - 8943
反应条件
1.1: 76 percent / Bu3SnH; AIBN / toluene / 12 h / 75 °C 2.1: 100 percent / LiOH*H2O; H2O2 / tetrahydrofuran; H2O / 1 h / 0 °C 3.1: 0.023 g / LiAlH4 / diethyl ether / 0 - 20 °C 4.1: 86 percent / DCC; DMAP / CH2Cl2 / 1 h / 0 °C 5.1: disiamylborane / tetrahydrofuran / 0 - 20 °C 5.2: 74 percent / H2O2; NaOH / tetrahydrofuran; H2O / 0.33 h / 10 - 20 °C 6.1: 89 percent / pyridine / 12 h / 0 - 20 °C 7.1: 88 percent / MsN3; Et3N / acetonitrile / 10 h / 20 °C 8.1: 87 percent / Rh2(OAc)4 / CH2Cl2 / 14 h / Heating 9.1: 84 percent / NaCl; H2O / dimethylsulfoxide / 12 h / 110 °C 10.1: 93 percent / Bu4NF / tetrahydrofuran / 0.67 h / 20 °C 11.1: 98 percent / Jones reagent / acetone / 0 °C 12.1: DCC / CH2Cl2 / 1 h / 0 °C 12.2: 67 percent / CH2Cl2 / 15 h / 20 °C 13.1: 92 percent / LiBH4 / tetrahydrofuran; methanol / 48 h / 20 °C 14.1: 92 percent / imidazole / dimethylformamide / 16 h / -20 - 20 °C 15.1: Et3N; Py*SO3 / dimethylsulfoxide / 60 h / 20 °C 15.2: 18.7 mg / TFA / CH2Cl2 / 16 h / -42 - 20 °C 16.1: 96 percent / Me3SiCl / methanol / 3 h / 0 - 20 °C 17.1: 30 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Heating 18.1: Py*SO3; Et3N / dimethylsulfoxide / 20 h / 20 °C 19.1: 2 mg / NMMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 3 h / 20 °C View Scheme
参考文献
Wee; Yu
Journal of Organic Chemistry, 2001 , vol. 66, # 26 p. 8935 - 8943
反应条件
1.1: 0.023 g / LiAlH4 / diethyl ether / 0 - 20 °C 2.1: 86 percent / DCC; DMAP / CH2Cl2 / 1 h / 0 °C 3.1: disiamylborane / tetrahydrofuran / 0 - 20 °C 3.2: 74 percent / H2O2; NaOH / tetrahydrofuran; H2O / 0.33 h / 10 - 20 °C 4.1: 89 percent / pyridine / 12 h / 0 - 20 °C 5.1: 88 percent / MsN3; Et3N / acetonitrile / 10 h / 20 °C 6.1: 87 percent / Rh2(OAc)4 / CH2Cl2 / 14 h / Heating 7.1: 84 percent / NaCl; H2O / dimethylsulfoxide / 12 h / 110 °C 8.1: 93 percent / Bu4NF / tetrahydrofuran / 0.67 h / 20 °C 9.1: 98 percent / Jones reagent / acetone / 0 °C 10.1: DCC / CH2Cl2 / 1 h / 0 °C 10.2: 67 percent / CH2Cl2 / 15 h / 20 °C 11.1: 92 percent / LiBH4 / tetrahydrofuran; methanol / 48 h / 20 °C 12.1: 92 percent / imidazole / dimethylformamide / 16 h / -20 - 20 °C 13.1: Et3N; Py*SO3 / dimethylsulfoxide / 60 h / 20 °C 13.2: 18.7 mg / TFA / CH2Cl2 / 16 h / -42 - 20 °C 14.1: 96 percent / Me3SiCl / methanol / 3 h / 0 - 20 °C 15.1: 30 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Heating 16.1: Py*SO3; Et3N / dimethylsulfoxide / 20 h / 20 °C 17.1: 2 mg / NMMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 3 h / 20 °C View Scheme
参考文献
Wee, Andrew G.H.; Yu, Qing
Tetrahedron Letters, 2000 , vol. 41, # 5 p. 587 - 590
反应条件
1.1: Bu2BOTf; Et3N / CH2Cl2 / 0.5 h / 0 °C 1.2: 52 percent / CH2Cl2 / -78 - 20 °C 2.1: 92 percent / DMAP; pyridine / CH2Cl2 / 3 h / 20 °C 3.1: 76 percent / Bu3SnH; AIBN / toluene / 12 h / 75 °C 4.1: 100 percent / LiOH*H2O; H2O2 / tetrahydrofuran; H2O / 1 h / 0 °C 5.1: 0.023 g / LiAlH4 / diethyl ether / 0 - 20 °C 6.1: 86 percent / DCC; DMAP / CH2Cl2 / 1 h / 0 °C 7.1: disiamylborane / tetrahydrofuran / 0 - 20 °C 7.2: 74 percent / H2O2; NaOH / tetrahydrofuran; H2O / 0.33 h / 10 - 20 °C 8.1: 89 percent / pyridine / 12 h / 0 - 20 °C 9.1: 88 percent / MsN3; Et3N / acetonitrile / 10 h / 20 °C 10.1: 87 percent / Rh2(OAc)4 / CH2Cl2 / 14 h / Heating 11.1: 84 percent / NaCl; H2O / dimethylsulfoxide / 12 h / 110 °C 12.1: 93 percent / Bu4NF / tetrahydrofuran / 0.67 h / 20 °C 13.1: 98 percent / Jones reagent / acetone / 0 °C 14.1: DCC / CH2Cl2 / 1 h / 0 °C 14.2: 67 percent / CH2Cl2 / 15 h / 20 °C 15.1: 92 percent / LiBH4 / tetrahydrofuran; methanol / 48 h / 20 °C 16.1: 92 percent / imidazole / dimethylformamide / 16 h / -20 - 20 °C 17.1: Et3N; Py*SO3 / dimethylsulfoxide / 60 h / 20 °C 17.2: 18.7 mg / TFA / CH2Cl2 / 16 h / -42 - 20 °C 18.1: 96 percent / Me3SiCl / methanol / 3 h / 0 - 20 °C 19.1: 30 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Heating 20.1: Py*SO3; Et3N / dimethylsulfoxide / 20 h / 20 °C 21.1: 2 mg / NMMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 3 h / 20 °C View Scheme
参考文献
Wee; Yu
Journal of Organic Chemistry, 2001 , vol. 66, # 26 p. 8935 - 8943
