(6E,10E)-7,11,15-三甲基-3-氧代十六碳-6,10,14-三烯酸乙酯(异构体混合物)合成路线 (共 7 条)
反应条件
1: ethyl acetoacetate With sodium hydride in tetrahydrofuran T=0°C; 0.25 h; Inert atmosphere; 2: With n-butyllithium in tetrahydrofuran T=0°C; 0.25 h; Inert atmosphere; 3: (E,E)-3,7,11-trimethyl-2,6,10-dodecatrienyl bromide in tetrahydrofuran T=0°C; 1.5 h; Inert atmosphere;
参考文献
Gampe, Christian M.; Tsukamoto, Hirokazu; Wang, Tsung-Shing Andrew; Walker, Suzanne; Kahne, Daniel
Tetrahedron, 2011 , vol. 67, # 51 p. 9771 - 9778
反应条件
1: NaCH(CO2Et)COCH3 With n-butyllithium in tetrahydrofuran; hexane T=0°C; 0.75 h; Inert atmosphere; 2: (E,E)-3,7,11-trimethyl-2,6,10-dodecatrienyl bromide in tetrahydrofuran; hexane T=0°C; Inert atmosphere; 3: With dipotassium hydrogenphosphate in tetrahydrofuran; hexane
参考文献
Duez, Stephanie; Coudray, Laetitia; Mouray, Elisabeth; Grellier, Philippe; Dubois, Joelle
Bioorganic and Medicinal Chemistry, 2010 , vol. 18, # 2 p. 543 - 556
反应条件
1: enolate sodique de l'acetylacetate d'ethyle With n-butyllithium in tetrahydrofuran; hexane T=0°C; Metallation; 0.333333 h; 2: (E,E)-3,7,11-trimethyl-2,6,10-dodecatrienyl bromide in tetrahydrofuran; cyclohexane Alkylation; 0.5 h;
参考文献
Gibbs, Barbara S.; Zahn, Todd J.; Mu, YongQi; Sebolt-Leopold, Judith S.; Gibbs, Richard A.
Journal of Medicinal Chemistry, 1999 , vol. 42, # 19 p. 3800 - 3808
参考文献
Gopalan; Prieto; Mueller; Peters
Tetrahedron Letters, 1992 , vol. 33, # 13 p. 1679 - 1682
反应条件
1: 58 percent / KH / tetrahydrofuran 2: 82 percent / bis(benzonitrile)palladium(II) chloride; triphenylarsine; Ag2O / K3PO4*nH2O / dioxane / 5 h / 20 °C 3: 72 percent / diisobutylaluminum hydride / toluene / 1 h / -78 °C View Scheme
参考文献
Mu, YongQi; Eubanks, Lisa M; Poulter, C Dale; Gibbs, Richard A
Bioorganic and medicinal chemistry, 2002 , vol. 10, # 5 p. 1207 - 1219
反应条件
1: 4-(N,N-dimethlyamino)pyridine; N,N'-dimethyl-N,N'-propyleneurea; triethylamine / 3 h / -30 - 20 °C / Inert atmosphere 2: iron (III) acetylacetonate / tetrahydrofuran; 1-methyl-pyrrolidin-2-one / 0.5 h / -40 - -20 °C / Inert atmosphere 3: diisobutylaluminium hydride / toluene / 1 h / -70 °C / Inert atmosphere View Scheme
参考文献
Lupoli, Tania J.; Tsukamoto, Hirokazu; Doud, Emma H.; Wang, Tsung-Shing Andrew; Walker, Suzanne; Kahne, Daniel
Journal of the American Chemical Society, 2011 , vol. 133, # 28 p. 10748 - 10751
反应条件
sodium hydroxide in tetrahydrofuran T=20 - 60°C;
参考文献
Organic Letters, , vol. 6, # 16 p. 2697 - 2700