Fagomine; 桑叶生物碱; (2R,3R,4R)-2-羟甲基哌啶-3,4-二醇合成路线 （共 56 条）
反应条件
1: 53 percent / aq. sodium bicarbonate / diethyl ether / 18 h 2: 87 percent / aq. TFA / 0.33 h / Ambient temperature 3: 97 percent / NaBH4 / ethanol; H2O / 0.33 h 4: H2, HOAc / Pd black / 18 h / 760 Torr View Scheme
参考文献
Tetrahedron Asymmetry, , vol. 1, # 2 p. 119 - 136
反应条件
1.1: 97 percent / Cl2(Cy3P2)Ru=CHPh / CH2Cl2 / 2 h / 20 °C 2.1: 45 percent / Na2EDTA; CF3COCH3; NaHCO3 / Oxone / acetonitrile / 1.5 h / 0 °C 3.1: 78 percent / Super-Hydride / tetrahydrofuran / 3 h / 0 °C 4.1: HCl / methanol; H2O / 2 h / 60 °C 4.2: 83 percent / DOWEX-50wX8 View Scheme
参考文献
Tetrahedron, , vol. 60, # 37 p. 8199 - 8205
反应条件
1: 76 percent / azobisisobutyronitrile, tri-n-butyltin hydride / toluene / 24 h / 75 °C 2: 1.) 50percent aq. trifluoroacetic acid; 2.) sodium borohydride / 1.) 30 min.; 2.) ethanol, room temp., 1 h. 3: 74 percent / hydrogen / 10percent palladium hydroxide on charcoal / ethanol / 12 h View Scheme
参考文献
Tetrahedron, , vol. 43, # 5 p. 979 - 990
反应条件
1: sodium methoxide / Heating 2: methanol / Dowex 50W-X8 resin (H+ form) / Heating 3: pyridine / CH2Cl2 / 0.33 h / -20 °C 4: NaN3 / dimethylformamide / 48 h / 50 °C 5: methanol / sodium methylate / Ambient temperature 6: pyridine / 6 h / Ambient temperature 8: pyridine / -20 °C 9: 1) lithium triethylborohydride, 2) benzyl chloroformate / 1) tetrahydrofuran 10: H2O / CF3COOH / 1 h / Ambient temperature 11: NaBH4 / ethanol; H2O 12: H2 / palladium hydroxide / ethanol View Scheme
参考文献
Tetrahedron Letters, , vol. 26, # 11 p. 1469 - 1472
反应条件
1: methanol / 0.5percent HCl / Ambient temperature 2: sodium methoxide / Heating 3: methanol / Dowex 50W-X8 resin (H+ form) / Heating 4: pyridine / CH2Cl2 / 0.33 h / -20 °C 5: NaN3 / dimethylformamide / 48 h / 50 °C 6: methanol / sodium methylate / Ambient temperature 7: pyridine / 6 h / Ambient temperature 9: pyridine / -20 °C 10: 1) lithium triethylborohydride, 2) benzyl chloroformate / 1) tetrahydrofuran 11: H2O / CF3COOH / 1 h / Ambient temperature 12: NaBH4 / ethanol; H2O 13: H2 / palladium hydroxide / ethanol View Scheme
参考文献
Tetrahedron Letters, , vol. 26, # 11 p. 1469 - 1472
反应条件
1: NaBH4 / ethanol; H2O 2: H2 / palladium hydroxide / ethanol View Scheme
参考文献
Tetrahedron Letters, , vol. 26, # 11 p. 1469 - 1472
反应条件
1: NaN3 / dimethylformamide / 48 h / 50 °C 2: methanol / sodium methylate / Ambient temperature 3: pyridine / 6 h / Ambient temperature 5: pyridine / -20 °C 6: 1) lithium triethylborohydride, 2) benzyl chloroformate / 1) tetrahydrofuran 7: H2O / CF3COOH / 1 h / Ambient temperature 8: NaBH4 / ethanol; H2O 9: H2 / palladium hydroxide / ethanol View Scheme
参考文献
Tetrahedron Letters, , vol. 26, # 11 p. 1469 - 1472
反应条件
2: pyridine / -20 °C 3: 1) lithium triethylborohydride, 2) benzyl chloroformate / 1) tetrahydrofuran 4: H2O / CF3COOH / 1 h / Ambient temperature 5: NaBH4 / ethanol; H2O 6: H2 / palladium hydroxide / ethanol View Scheme
参考文献
Tetrahedron Letters, , vol. 26, # 11 p. 1469 - 1472
反应条件
1: benzylation 2: methanol / 0.5percent HCl / Ambient temperature 3: sodium methoxide / Heating 4: methanol / Dowex 50W-X8 resin (H+ form) / Heating 5: pyridine / CH2Cl2 / 0.33 h / -20 °C 6: NaN3 / dimethylformamide / 48 h / 50 °C 7: methanol / sodium methylate / Ambient temperature 8: pyridine / 6 h / Ambient temperature 10: pyridine / -20 °C 11: 1) lithium triethylborohydride, 2) benzyl chloroformate / 1) tetrahydrofuran 12: H2O / CF3COOH / 1 h / Ambient temperature 13: NaBH4 / ethanol; H2O 14: H2 / palladium hydroxide / ethanol View Scheme
参考文献
Tetrahedron Letters, , vol. 26, # 11 p. 1469 - 1472
反应条件
1: 87 percent / aq. TFA / 0.33 h / Ambient temperature 2: 97 percent / NaBH4 / ethanol; H2O / 0.33 h 3: H2, HOAc / Pd black / 18 h / 760 Torr View Scheme
参考文献
Tetrahedron Asymmetry, , vol. 1, # 2 p. 119 - 136
