5-羟基-2-癸烯酸-δ-内酯合成路线 （共 63 条）
反应条件
1.1: 71 percent / diisobutylaluminium hydride / CH2Cl2 / 3.5 h / -78 °C 2.1: LDA / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C 2.2: 87 percent / tetrahydrofuran; diethyl ether / 3 h / -78 - 0 °C 3.1: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C 4.1: 73 percent / quinoline; hydrogen / palladium on BaSO4 / ethyl acetate / 3 h / 20 °C / 750.06 Torr 5.1: 82 percent / triethylamine / CH2Cl2 / 0 - 20 °C 6.1: 78 percent / bis(tricyclohexylphosphine) benzylidene Ru(IV) dichloride / CH2Cl2 / 6 h / Heating View Scheme
参考文献
Fournier, Lycia; Kocienski, Philip; Pons, Jean-Marc
Tetrahedron, 2004 , vol. 60, # 7 p. 1659 - 1663
反应条件
1.1: P(OPh)3 / Pd(OAc)2 / tetrahydrofuran 1.2: 70 percent / tetrahydrofuran / 1 h / -78 °C 2.1: 76 percent / KF / dimethylsulfoxide View Scheme
参考文献
Marion; Le Fol; Courillon; Malacria
Synlett, 2001 , # 1 p. 138 - 140
反应条件
1: 71 percent / diethyl ether; pentane / 1 h / -100 °C 2: 82 percent / Et3N / CH2Cl2 / 4 h / 20 °C 3: 84 percent / bis(tricyclohexylphosphine)benzylidene Ru(IV) dichloride / CH2Cl2 / 6 h / Heating View Scheme
参考文献
Bartlett, Sean; Boese, Dietrich; Ghori, Daniel; Mechsner, Bastian; Pietruszka, Joerg
Synthesis (Germany), 2013 , vol. 45, # 8 art. no. SS-2013-T0089-OP, p. 1106 - 1114
反应条件
1: 90 percent / pyridine, N,N-dimethyl-4-aminopyridine (DMAP) / CH2Cl2 / 4 h / Ambient temperature 2: 44 percent / 20 h / 0.1 M phosphate buffer (pH 7.0), Pseudomonas sp. (SAM II) lipase 3: 1.) trimethyloxonium tetrafluoroborate, 2.) aq. NaOH / 1.) CH2Cl2, RT, 2 h, 2.) CH2Cl2, 2.5 h 4: 1.) n-butyllithium, 2.) BF3*OEt2 / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 deg C, 1.5 h 5: 92 percent / H2, quinoline / Lindlar catalyst / ethyl acetate / 760 Torr 6: 89 percent / p-TsOH, water / toluene / 1.5 h / Heating View Scheme
参考文献
Haase, Bernhard; Schneider, Manfred P.
Tetrahedron: Asymmetry, 1993 , vol. 4, # 5 p. 1017 - 1026
反应条件
1: 1.) trimethyloxonium tetrafluoroborate, 2.) aq. NaOH / 1.) CH2Cl2, RT, 2 h, 2.) CH2Cl2, 2.5 h 2: 1.) n-butyllithium, 2.) BF3*OEt2 / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 deg C, 1.5 h 3: 92 percent / H2, quinoline / Lindlar catalyst / ethyl acetate / 760 Torr 4: 89 percent / p-TsOH, water / toluene / 1.5 h / Heating View Scheme
参考文献
Haase, Bernhard; Schneider, Manfred P.
Tetrahedron: Asymmetry, 1993 , vol. 4, # 5 p. 1017 - 1026
反应条件
1: 44 percent / 20 h / 0.1 M phosphate buffer (pH 7.0), Pseudomonas sp. (SAM II) lipase 2: 1.) trimethyloxonium tetrafluoroborate, 2.) aq. NaOH / 1.) CH2Cl2, RT, 2 h, 2.) CH2Cl2, 2.5 h 3: 1.) n-butyllithium, 2.) BF3*OEt2 / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 deg C, 1.5 h 4: 92 percent / H2, quinoline / Lindlar catalyst / ethyl acetate / 760 Torr 5: 89 percent / p-TsOH, water / toluene / 1.5 h / Heating View Scheme
参考文献
Haase, Bernhard; Schneider, Manfred P.
Tetrahedron: Asymmetry, 1993 , vol. 4, # 5 p. 1017 - 1026
反应条件
1: 94.8 percent / dimethylsulfoxide / Ambient temperature 2: 85.1 percent / PdCl2, CuCl2, NaOAc / 760 Torr / Ambient temperature 3: H2, quinoline / Lindlar catalyst / ethyl acetate / Ambient temperature 4: concd HCl / methanol / Ambient temperature View Scheme
参考文献
Takano; Setoh; Ogasawara
Tetrahedron Asymmetry, 1992 , vol. 3, # 4 p. 533 - 534
反应条件
1: 68 percent / (PPh3)3RuCl2 / benzene / 72 h / Ambient temperature 2: 94 percent / H2 / Pd/C / ethyl acetate / 8 h / 760 Torr / Ambient temperature 3: 77 percent / p-toluenesulfonic acid / benzene / 5 h / Heating View Scheme
参考文献
Romeyke, Yvonne; Keller, Martin; Kluge, Heinz; Grabley, Susanne; Hammann, Peter
Tetrahedron, 1991 , vol. 47, # 20 p. 3335 - 3346
反应条件
1: 1.) Et3B 2.) NaBH4 / 1.) THF, r.t., 15 min 2.) MeOH, -70 deg C, 3 h 2: 68 percent / (PPh3)3RuCl2 / benzene / 72 h / Ambient temperature 3: 94 percent / H2 / Pd/C / ethyl acetate / 8 h / 760 Torr / Ambient temperature 4: 77 percent / p-toluenesulfonic acid / benzene / 5 h / Heating View Scheme
参考文献
Romeyke, Yvonne; Keller, Martin; Kluge, Heinz; Grabley, Susanne; Hammann, Peter
Tetrahedron, 1991 , vol. 47, # 20 p. 3335 - 3346
反应条件
1: 94 percent / H2 / Pd/C / ethyl acetate / 8 h / 760 Torr / Ambient temperature 2: 77 percent / p-toluenesulfonic acid / benzene / 5 h / Heating View Scheme
参考文献
Romeyke, Yvonne; Keller, Martin; Kluge, Heinz; Grabley, Susanne; Hammann, Peter
Tetrahedron, 1991 , vol. 47, # 20 p. 3335 - 3346
