Makaluvamine A合成路线 (共 32 条)
反应条件
1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 °C / |Inert atmosphere
2: water; sodium hydroxide / methanol / 0.5 h / |Reflux; |Inert atmosphere
3: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / 0 °C / |Inert atmosphere
4: salenCo(II); oxygen / N,N-dimethyl-formamide / 1 h / 20 °C / |Inert atmosphere
5: 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: water; sodium hydroxide / methanol / 0.5 h / |Reflux; |Inert atmosphere
2: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / 0 °C / |Inert atmosphere
3: salenCo(II); oxygen / N,N-dimethyl-formamide / 1 h / 20 °C / |Inert atmosphere
4: 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: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / 0 °C / |Inert atmosphere
2: salenCo(II); oxygen / N,N-dimethyl-formamide / 1 h / 20 °C / |Inert atmosphere
3: 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: acetonitrile / 4 h / |Reflux; |Inert atmosphere
2: AlCl3, aluminium chloride; lithium aluminium tetrahydride / diethyl ether / 0.33 h / 0 °C / |Inert atmosphere
3: triethylamine / 1,2-dichloro-ethane / 10 h / 20 °C / |Inert atmosphere
4: sodium iodide / acetone / 5 h / |Inert atmosphere; |Reflux
5: n-butyllithium; 2,2,6,6-tetramethyl-piperidine / tetrahydrofuran; hexane / 0.5 h / -78 - 0 °C / |Inert atmosphere; |Schlenk technique
6: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 0.33 h / 0 °C / |Inert atmosphere
7: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 °C / |Inert atmosphere
8: water; sodium hydroxide / methanol / 0.5 h / |Reflux; |Inert atmosphere
9: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / 0 °C / |Inert atmosphere
10: salenCo(II); oxygen / N,N-dimethyl-formamide / 1 h / 20 °C / |Inert atmosphere
11: 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: 96 percent / aq. acetic acid / 15 h / Ambient temperature
2: 97 percent / NaH / tetrahydrofuran / 0 °C
3: 1.) t-BuLi, 2.) Cl3CCCl3 / 1.) ether, pentane, -78 deg C, 20 min, 0 deg C, 1 h, 2.) ether, pentane, -78 deg C to rt
4: benzene / Ambient temperature
5: 3.46 g / TBAF / tetrahydrofuran / 1 h
6: 99 percent / NaH / tetrahydrofuran / 0.5 h / 0 °C
7: 52 percent / BH3*THF / tetrahydrofuran / 16 h / Ambient temperature; other solvent, reagent, temperature, reaction time
8: 54 percent / LDA / tetrahydrofuran / -50 - 0 °C / other reagent, temperature, reaction time
9: O2, salcomine / dimethylformamide / 2 h / Ambient temperature
10: NH4Cl / methanol / 13 h / Ambient temperature
View Scheme
参考文献
Iwao, Masatomo; Motoi, Osamu; Fukuda, Tsutomu; Ishibashi, Fumito
Tetrahedron, 1998 , vol. 54, # 31 p. 8999 - 9010
反应条件
1: 97 percent / NaH / tetrahydrofuran / 0 °C
2: 1.) t-BuLi, 2.) Cl3CCCl3 / 1.) ether, pentane, -78 deg C, 20 min, 0 deg C, 1 h, 2.) ether, pentane, -78 deg C to rt
3: benzene / Ambient temperature
4: 3.46 g / TBAF / tetrahydrofuran / 1 h
5: 99 percent / NaH / tetrahydrofuran / 0.5 h / 0 °C
6: 52 percent / BH3*THF / tetrahydrofuran / 16 h / Ambient temperature; other solvent, reagent, temperature, reaction time
7: 54 percent / LDA / tetrahydrofuran / -50 - 0 °C / other reagent, temperature, reaction time
8: O2, salcomine / dimethylformamide / 2 h / Ambient temperature
9: NH4Cl / methanol / 13 h / Ambient temperature
View Scheme
参考文献
Iwao, Masatomo; Motoi, Osamu; Fukuda, Tsutomu; Ishibashi, Fumito
Tetrahedron, 1998 , vol. 54, # 31 p. 8999 - 9010
反应条件
1: 54 percent / LDA / tetrahydrofuran / -50 - 0 °C / other reagent, temperature, reaction time
2: O2, salcomine / dimethylformamide / 2 h / Ambient temperature
3: NH4Cl / methanol / 13 h / Ambient temperature
View Scheme
参考文献
Iwao, Masatomo; Motoi, Osamu; Fukuda, Tsutomu; Ishibashi, Fumito
Tetrahedron, 1998 , vol. 54, # 31 p. 8999 - 9010
反应条件
1: 52 percent / BH3*THF / tetrahydrofuran / 16 h / Ambient temperature; other solvent, reagent, temperature, reaction time
2: 54 percent / LDA / tetrahydrofuran / -50 - 0 °C / other reagent, temperature, reaction time
3: O2, salcomine / dimethylformamide / 2 h / Ambient temperature
4: NH4Cl / methanol / 13 h / Ambient temperature
View Scheme
参考文献
Iwao, Masatomo; Motoi, Osamu; Fukuda, Tsutomu; Ishibashi, Fumito
Tetrahedron, 1998 , vol. 54, # 31 p. 8999 - 9010
反应条件
1: DCC / tetrahydrofuran / -15 deg C, 1.5 h then to r.t., overnight
2: 1.) BH3*SMe2; 2.) CAN / 1.) THF, r.t., 3 h; 2.) 60percent aq. CH3CN, 0 deg C, 5 min
3: 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: 10M KOH / ethanol / 0.5 h / Ambient temperature
2: DCC / tetrahydrofuran / -15 deg C, 1.5 h then to r.t., overnight
3: 1.) BH3*SMe2; 2.) CAN / 1.) THF, r.t., 3 h; 2.) 60percent aq. CH3CN, 0 deg C, 5 min
4: 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