Makaluvamine A合成路线 (共 32 条)
反应条件
1: 73 percent / TFA, t-BuI, I2, FeCl2 / dimethylsulfoxide / 5 h / 80 - 85 °C
2: 93 percent / HCl / diethyl ether / 65 h / Heating
3: 86 percent / NiCl2, BaBH4 / methanol / 0.08 h / 50 °C
4: 64 percent / aq. HCl / tetrahydrofuran / 1 h / 40 °C
5: CH2Cl2 / 15 h / Ambient temperature
6: 1.) NaH / 1.) THF, room temperature 45 min, reflux - 15 min, 2.) THF, 14 h
7: 80 percent / TFA / CH2Cl2 / 1.5 h / Ambient temperature
8: 60 percent / ceric ammonium nitrate
9: 98 percent / NH4Cl
View Scheme
参考文献
Roberts, David; Joule, John A.; Antonieta Bros; Alvarez, Mercedes
Journal of Organic Chemistry, 1997 , vol. 62, # 3 p. 568 - 577
反应条件
1: 1.) AcOH, FeCl3, 2.) AcOH / 1.) 60 deg C, 5 min, 2.) reflux, 5 h
2: 63 percent / HNO3 / 1.) -50-(-40) deg C, 1 h, 2.) -30 deg C, 25 min
3: 73 percent / TFA, t-BuI, I2, FeCl2 / dimethylsulfoxide / 5 h / 80 - 85 °C
4: 93 percent / HCl / diethyl ether / 65 h / Heating
5: 86 percent / NiCl2, BaBH4 / methanol / 0.08 h / 50 °C
6: 64 percent / aq. HCl / tetrahydrofuran / 1 h / 40 °C
7: CH2Cl2 / 15 h / Ambient temperature
8: 1.) NaH / 1.) THF, room temperature 45 min, reflux - 15 min, 2.) THF, 14 h
9: 80 percent / TFA / CH2Cl2 / 1.5 h / Ambient temperature
10: 60 percent / ceric ammonium nitrate
11: 98 percent / NH4Cl
View Scheme
参考文献
Roberts, David; Joule, John A.; Antonieta Bros; Alvarez, Mercedes
Journal of Organic Chemistry, 1997 , vol. 62, # 3 p. 568 - 577
反应条件
1: CH2Cl2 / 15 h / Ambient temperature
2: 1.) NaH / 1.) THF, room temperature 45 min, reflux - 15 min, 2.) THF, 14 h
3: 80 percent / TFA / CH2Cl2 / 1.5 h / Ambient temperature
4: 60 percent / ceric ammonium nitrate
5: 98 percent / NH4Cl
View Scheme
参考文献
Roberts, David; Joule, John A.; Antonieta Bros; Alvarez, Mercedes
Journal of Organic Chemistry, 1997 , vol. 62, # 3 p. 568 - 577
反应条件
1: 64 percent / aq. HCl / tetrahydrofuran / 1 h / 40 °C
2: CH2Cl2 / 15 h / Ambient temperature
3: 1.) NaH / 1.) THF, room temperature 45 min, reflux - 15 min, 2.) THF, 14 h
4: 80 percent / TFA / CH2Cl2 / 1.5 h / Ambient temperature
5: 60 percent / ceric ammonium nitrate
6: 98 percent / NH4Cl
View Scheme
参考文献
Roberts, David; Joule, John A.; Antonieta Bros; Alvarez, Mercedes
Journal of Organic Chemistry, 1997 , vol. 62, # 3 p. 568 - 577
反应条件
1: 80 percent / TFA / CH2Cl2 / 1.5 h / Ambient temperature
2: 60 percent / ceric ammonium nitrate
3: 98 percent / NH4Cl
View Scheme
参考文献
Roberts, David; Joule, John A.; Antonieta Bros; Alvarez, Mercedes
Journal of Organic Chemistry, 1997 , vol. 62, # 3 p. 568 - 577
反应条件
1: 1.) NaH / 1.) THF, room temperature 45 min, reflux - 15 min, 2.) THF, 14 h
2: 80 percent / TFA / CH2Cl2 / 1.5 h / Ambient temperature
3: 60 percent / ceric ammonium nitrate
4: 98 percent / NH4Cl
View Scheme
参考文献
Roberts, David; Joule, John A.; Antonieta Bros; Alvarez, Mercedes
Journal of Organic Chemistry, 1997 , vol. 62, # 3 p. 568 - 577
反应条件
1: 1.) BH3*SMe2; 2.) CAN / 1.) THF, r.t., 3 h; 2.) 60percent aq. CH3CN, 0 deg C, 5 min
2: 98 percent / NH4Cl / methanol / Ambient temperature
View Scheme
参考文献
Izawa, Takao; Nishiyama, Shigeru; Yamamura, Shosuke
Tetrahedron, 1994 , vol. 50, # 48 p. 13593 - 13600
反应条件
1: sodium iodide / acetone / 5 h / |Inert atmosphere; |Reflux
2: n-butyllithium; 2,2,6,6-tetramethyl-piperidine / tetrahydrofuran; hexane / 0.5 h / -78 - 0 °C / |Inert atmosphere; |Schlenk technique
3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 0.33 h / 0 °C / |Inert atmosphere
4: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 °C / |Inert atmosphere
5: water; sodium hydroxide / methanol / 0.5 h / |Reflux; |Inert atmosphere
6: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / 0 °C / |Inert atmosphere
7: salenCo(II); oxygen / N,N-dimethyl-formamide / 1 h / 20 °C / |Inert atmosphere
8: ammonium chloride / methanol / 13 h / 20 °C / |Inert atmosphere
View Scheme
参考文献
Oshiyama, Takashi; Satoh, Takahito; Okano, Kentaro; Tokuyama, Hidetoshi
Tetrahedron, 2012 , vol. 68, # 46 p. 9376 - 9383,8
Title/Abstract Full Text Show Details
Oshiyama, Takashi; Satoh, Takahito; Okano, Kentaro; Tokuyama, Hidetoshi
Tetrahedron, 2012 , vol. 68, # 46 p. 9376 - 9383
反应条件
1: n-butyllithium; 2,2,6,6-tetramethyl-piperidine / tetrahydrofuran; hexane / 0.5 h / -78 - 0 °C / |Inert atmosphere; |Schlenk technique
2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 0.33 h / 0 °C / |Inert atmosphere
3: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 °C / |Inert atmosphere
4: water; sodium hydroxide / methanol / 0.5 h / |Reflux; |Inert atmosphere
5: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / 0 °C / |Inert atmosphere
6: salenCo(II); oxygen / N,N-dimethyl-formamide / 1 h / 20 °C / |Inert atmosphere
7: ammonium chloride / methanol / 13 h / 20 °C / |Inert atmosphere
View Scheme
参考文献
Oshiyama, Takashi; Satoh, Takahito; Okano, Kentaro; Tokuyama, Hidetoshi
Tetrahedron, 2012 , vol. 68, # 46 p. 9376 - 9383,8
Title/Abstract Full Text Show Details
Oshiyama, Takashi; Satoh, Takahito; Okano, Kentaro; Tokuyama, Hidetoshi
Tetrahedron, 2012 , vol. 68, # 46 p. 9376 - 9383
反应条件
1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 0.33 h / 0 °C / |Inert atmosphere
2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 °C / |Inert atmosphere
3: water; sodium hydroxide / methanol / 0.5 h / |Reflux; |Inert atmosphere
4: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / 0 °C / |Inert atmosphere
5: salenCo(II); oxygen / N,N-dimethyl-formamide / 1 h / 20 °C / |Inert atmosphere
6: ammonium chloride / methanol / 13 h / 20 °C / |Inert atmosphere
View Scheme
参考文献
Oshiyama, Takashi; Satoh, Takahito; Okano, Kentaro; Tokuyama, Hidetoshi
Tetrahedron, 2012 , vol. 68, # 46 p. 9376 - 9383,8
Title/Abstract Full Text Show Details
Oshiyama, Takashi; Satoh, Takahito; Okano, Kentaro; Tokuyama, Hidetoshi
Tetrahedron, 2012 , vol. 68, # 46 p. 9376 - 9383