1-羟基环己烷丙酸 gamma-内酯合成路线 （共 73 条）
反应条件
1: 99 percent / 96 percent H2SO4 / 72 h / Heating
2: 62 percent / LiAlH4 / diethyl ether / 3 h / 0 - 20 °C
3: 71 percent / pyridine / 24 h / 0 - 5 °C
4: 54 percent / NaI / acetone / 24 h / Heating
5: 94 percent / NaCN / 72 h / 80 °C
6: 59 percent / 96 percent H2SO4 / methanol / 24 h / Heating
View Scheme
参考文献
Crotti, Paolo; Badalassi, Fabrizio; Di Bussolo, Valeria; Favero, Lucilla; Pineschi, Mauro
Tetrahedron, 2001 , vol. 57, # 40 p. 8559 - 8572
反应条件
1: 1.) LDA, Et2AlCl / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -35 deg C, 6 h
2: 86 percent / TsOH*H2O / CHCl3 / 24 h / Ambient temperature
View Scheme
参考文献
Taylor, Stephen K.; Chmiel, Nikolas H.; Mann, Emily E.; Silver, Michael E.; Vyvyan, James R.
Synthesis, 1998 , # 7 p. 1009 - 1014
反应条件
1: 80 percent / SnCl4 / benzene / 10 h / Ambient temperature
2: KOH/H2O / 30 h / Ambient temperature
3: 92 percent / ceric ammonium nitrate / acetonitrile; H2O / 1 h / Ambient temperature
View Scheme
参考文献
Salomon, Robert G.; Roy, Subhas; Salomon, Mary F.
Tetrahedron Letters, 1988 , vol. 29, # 7 p. 769 - 772
反应条件
1: KOH/H2O / 30 h / Ambient temperature
2: 92 percent / ceric ammonium nitrate / acetonitrile; H2O / 1 h / Ambient temperature
View Scheme
参考文献
Salomon, Robert G.; Roy, Subhas; Salomon, Mary F.
Tetrahedron Letters, 1988 , vol. 29, # 7 p. 769 - 772
反应条件
(3,1)-dirhodium(II) tetrakis[methyl 1-acetyl-2-oxoimidazoline-4(S)-carboxylate] in dichloromethane
Heating; Yield given. Yields of byproduct given;
参考文献
Doyle; Zhou; Raab; Roos
Tetrahedron Letters, 1995 , vol. 36, # 27 p. 4745 - 4748
反应条件
1: 9,10-dicyanoanthracene, 1,4-azabicyclooctane / methanol / 16 h / Irradiation
2: p-toluenesulfonic acid / CDCl3 / other solvent, other substrates
View Scheme
参考文献
Hofland, A.; Boer, Th. J.
Recueil des Travaux Chimiques des Pays-Bas, 1987 , vol. 106, # 11 p. 558 - 562
反应条件
potassium dichromate; diethyl ether; sulfuric acid
参考文献
Raunio; Schroeder
Journal of Organic Chemistry, 1957 , vol. 22, p. 570
反应条件
sodium dichromate; dimethylsulfide borane complex; sulfuric acid
1.) Et2O, a) -78 to 25 deg C, b) 25 deg C, 12 h, 2.) reflux, 1 h; Yield given. Multistep reaction;
参考文献
Mandal; Mahajan
Synthesis, 1991 , # 4 p. 311 - 313
反应条件
sulfuric acid; water; lithium diisopropyl amide
1.) LDA, -78 to 0 deg C, THF/hexane, 2.) THF, reflux; Yield given. Multistep reaction;
参考文献
Jacobson, Richard M.; Lahm, George P.; Clader, John W.
Journal of Organic Chemistry, 1980 , vol. 45, # 3 p. 395 - 405
反应条件
N,N,N',N',N'',N''-hexamethylphosphoric triamide; sec.-butyllithium; Sm(OTf)3
1.) THF, cyclohexane, room temperature, 1 h, 2.) THF, cyclohexane, room temperature, 1 h; Yield given. Multistep reaction;
参考文献
Fukuzawa, Shin-Ichi; Mutoh, Keisuke; Tsuchimoto, Teruhisa; Hiyama, Tamejiro
Journal of Organic Chemistry, 1996 , vol. 61, # 16 p. 5400 - 5405
