卡巴环素合成路线

卡巴环素合成路线（共 75 条）

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反应条件

1: 95 percent / H2 / napthalene*Cr(CO)3 / tetrahydrofuran / 23 h / 45 °C / 55163.1 Torr 2: 100 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 13 h / 23 °C 3: 100 percent / 10percent aq. NaOH / methanol / 13 h / 0 °C View Scheme

参考文献

Chemical and Pharmaceutical Bulletin, , vol. 39, # 2 p. 309 - 322

101314-27-6

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69552-46-1卡巴环素

反应条件

1: 90 percent / imidazole / dimethylformamide / 1 h / 23 °C 2: 95 percent / H2 / napthalene*Cr(CO)3 / tetrahydrofuran / 23 h / 45 °C / 55163.1 Torr 3: 100 percent / tetrabutylammonium fluoride (TBAF) / tetrahydrofuran / 13 h / 23 °C 4: 100 percent / 10percent aq. NaOH / methanol / 13 h / 0 °C View Scheme

参考文献

Chemical and Pharmaceutical Bulletin, , vol. 39, # 2 p. 309 - 322

73996-33-5

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69552-46-1卡巴环素

反应条件

RhCl(PPh3)3 Multistep reaction;

参考文献

Chemical & Pharmaceutical Bulletin, , vol. 32, # 9 p. 3768 - 3769

70870-94-9

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69552-46-1卡巴环素

反应条件

1: 0.74 g / pyridinium p-toluenesulphonate / CH2Cl2 / 3 h / Ambient temperature 2: 1.) lithium aluminium hydride; 2.) 10percent NaOH / 1.) ether, 1.5 H; 2.) water, 1 h 3: 2.67 g / NaOAc, pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature 4: 1.) NaH / 1.) THF, r.t., 30 min; 2.) THF, r.t., 30 min 5: 1.) NaBH4 / 1.) methanol, -15 deg C, 30 min; 2.) acetic acid-water-THF (3:1:1), 45 deg C, 3 h 6: 93 percent / pyridinium p-toluenesulphonate / CH2Cl2 / 3 h / Ambient temperature 7: 1.) NaCH2SOCH3 / 1.) DMSO, r.t., 30 min; 2.) DMSO, 45 deg C, 22 h 8: 79 percent / acetic acid; H2O; tetrahydrofuran / 3 h / 45 °C View Scheme

参考文献

Tetrahedron, , vol. 42, # 1 p. 435 - 444

102491-09-8

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69552-46-1卡巴环素

反应条件

1: 1.) NaBH4 / 1.) methanol, -15 deg C, 30 min; 2.) acetic acid-water-THF (3:1:1), 45 deg C, 3 h 2: 93 percent / pyridinium p-toluenesulphonate / CH2Cl2 / 3 h / Ambient temperature 3: 1.) NaCH2SOCH3 / 1.) DMSO, r.t., 30 min; 2.) DMSO, 45 deg C, 22 h 4: 79 percent / acetic acid; H2O; tetrahydrofuran / 3 h / 45 °C View Scheme

参考文献

Tetrahedron, , vol. 42, # 1 p. 435 - 444

70893-59-3

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反应条件

1: 76 percent / NaBH4 / ethanol / 1 h / -15 °C 2: 0.74 g / pyridinium p-toluenesulphonate / CH2Cl2 / 3 h / Ambient temperature 3: 1.) lithium aluminium hydride; 2.) 10percent NaOH / 1.) ether, 1.5 H; 2.) water, 1 h 4: 2.67 g / NaOAc, pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature 5: 1.) NaH / 1.) THF, r.t., 30 min; 2.) THF, r.t., 30 min 6: 1.) NaBH4 / 1.) methanol, -15 deg C, 30 min; 2.) acetic acid-water-THF (3:1:1), 45 deg C, 3 h 7: 93 percent / pyridinium p-toluenesulphonate / CH2Cl2 / 3 h / Ambient temperature 8: 1.) NaCH2SOCH3 / 1.) DMSO, r.t., 30 min; 2.) DMSO, 45 deg C, 22 h 9: 79 percent / acetic acid; H2O; tetrahydrofuran / 3 h / 45 °C View Scheme

参考文献

Tetrahedron, , vol. 42, # 1 p. 435 - 444

96244-89-2

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反应条件

1: 1.) NaH / 1.) THF, r.t., 30 min; 2.) THF, r.t., 30 min 2: 1.) NaBH4 / 1.) methanol, -15 deg C, 30 min; 2.) acetic acid-water-THF (3:1:1), 45 deg C, 3 h 3: 93 percent / pyridinium p-toluenesulphonate / CH2Cl2 / 3 h / Ambient temperature 4: 1.) NaCH2SOCH3 / 1.) DMSO, r.t., 30 min; 2.) DMSO, 45 deg C, 22 h 5: 79 percent / acetic acid; H2O; tetrahydrofuran / 3 h / 45 °C View Scheme

参考文献

Tetrahedron, , vol. 42, # 1 p. 435 - 444

105448-63-3

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69552-46-1卡巴环素

反应条件

1: 1.) lithium aluminium hydride; 2.) 10percent NaOH / 1.) ether, 1.5 H; 2.) water, 1 h 2: 2.67 g / NaOAc, pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature 3: 1.) NaH / 1.) THF, r.t., 30 min; 2.) THF, r.t., 30 min 4: 1.) NaBH4 / 1.) methanol, -15 deg C, 30 min; 2.) acetic acid-water-THF (3:1:1), 45 deg C, 3 h 5: 93 percent / pyridinium p-toluenesulphonate / CH2Cl2 / 3 h / Ambient temperature 6: 1.) NaCH2SOCH3 / 1.) DMSO, r.t., 30 min; 2.) DMSO, 45 deg C, 22 h 7: 79 percent / acetic acid; H2O; tetrahydrofuran / 3 h / 45 °C View Scheme

参考文献

Tetrahedron, , vol. 42, # 1 p. 435 - 444

74028-43-6

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69552-46-1卡巴环素

反应条件

1: 1.) Na / 1.) DMSO, 25 deg C (prep. of reagent), 2.) DMSO, 35 deg C, 16 h 2: O.5 N HCl / tetrahydrofuran / 0.17 h / 0 °C 3: diethyl ether 4: 98 percent / SO3*pyridine complex / dimethylsulfoxide; triethylamine / 0.25 h / Ambient temperature 5: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, RT, 1 h 6: 65percent AcOH / tetrahydrofuran / 0.75 h / 50 °C 7: 83 percent / diisobutylaluminum hydride, 2,6-di-t-butyl-4-methylphenol / 1.) toluene, 5 deg C, 1 h, 2.) toluene, -78 deg C (adding), up to -10 deg C within 2.5 h, then -10 deg C, 10 min 8: 96 percent / 5percent aq KOH / ethanol / 0.33 h / 50 °C View Scheme

参考文献

Tetrahedron, , vol. 37, # 25 p. 4391 - 4399

73996-05-1

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反应条件

1: 98 percent / SO3*pyridine complex / dimethylsulfoxide; triethylamine / 0.25 h / Ambient temperature 2: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, RT, 1 h 3: 65percent AcOH / tetrahydrofuran / 0.75 h / 50 °C 4: 83 percent / diisobutylaluminum hydride, 2,6-di-t-butyl-4-methylphenol / 1.) toluene, 5 deg C, 1 h, 2.) toluene, -78 deg C (adding), up to -10 deg C within 2.5 h, then -10 deg C, 10 min 5: 96 percent / 5percent aq KOH / ethanol / 0.33 h / 50 °C View Scheme

参考文献

Tetrahedron, , vol. 37, # 25 p. 4391 - 4399

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