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C27H21NO7
chelidonine
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In 1,4-dioxane at 20℃; for 19h; Reflux; Inert atmosphere; | 88% |
chelidonine
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran; 1,4-dioxane for 17h; Reflux; | 82% |
(-)-5-methyl-2,3:7,8-bis(methylenedioxy)-10b-triethylsilyloxy-4b,10b,11,12-tetrahydrobenzo[c]phenanthridin-6(5H)-one
chelidonine
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 7 h / 85 °C / Inert atmosphere 2.1: dichloromethane / 27 h / 0 - 20 °C / Inert atmosphere 3.1: water; sodium hydroxide / tetrahydrofuran / 16 h / 20 - 40 °C 4.1: toluene-4-sulfonic acid / methanol / 6 h / 20 °C / Inert atmosphere 4.2: 2 h / 0 °C / Inert atmosphere 5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 48 h / 110 °C 6.1: lithium aluminium tetrahydride / diethyl ether / 1 h / 50 °C / Inert atmosphere 7.1: platinum(IV) oxide; hydrogen / ethanol / 14 h / 20 °C / 760.05 Torr 8.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 22 h / 50 °C / Inert atmosphere View Scheme |
(-)-5-methyl-2,3:7,8-bis(methylenedioxy)-10b-triethylsilyloxy-4b,10b-dihydrobenzo[c]phenanthridin-6(5H)-one
chelidonine
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: dichloromethane / 27 h / 0 - 20 °C / Inert atmosphere 2.1: water; sodium hydroxide / tetrahydrofuran / 16 h / 20 - 40 °C 3.1: toluene-4-sulfonic acid / methanol / 6 h / 20 °C / Inert atmosphere 3.2: 2 h / 0 °C / Inert atmosphere 4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 48 h / 110 °C 5.1: lithium aluminium tetrahydride / diethyl ether / 1 h / 50 °C / Inert atmosphere 6.1: platinum(IV) oxide; hydrogen / ethanol / 14 h / 20 °C / 760.05 Torr 7.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 22 h / 50 °C / Inert atmosphere View Scheme |
(-)-12-(3-chlorobenzoyloxy)-11-hydroxy-5-methyl-2,3:7,8-bis(methylenedioxy)-10b-triethylsilyloxy-4b,5,6,10b,11,12-hexahydrobenzo[c]phenanthridin-6(5H)-one
chelidonine
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: water; sodium hydroxide / tetrahydrofuran / 16 h / 20 - 40 °C 2.1: toluene-4-sulfonic acid / methanol / 6 h / 20 °C / Inert atmosphere 2.2: 2 h / 0 °C / Inert atmosphere 3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 48 h / 110 °C 4.1: lithium aluminium tetrahydride / diethyl ether / 1 h / 50 °C / Inert atmosphere 5.1: platinum(IV) oxide; hydrogen / ethanol / 14 h / 20 °C / 760.05 Torr 6.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 22 h / 50 °C / Inert atmosphere View Scheme |
chelidonine
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: sodium tetrahydroborate; methanol / 0.5 h / 0 °C 2: potassium hydroxide / 2 h / 0 - 20 °C 3: triphenylphosphine; carbon tetrabromide / dichloromethane / 0.5 h / 0 - 20 °C 4: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 - 20 °C 5: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 1 h / 70 °C / Inert atmosphere 6: N-Bromosuccinimide; water / tetrahydrofuran / 1.5 h / 20 °C 7: potassium tert-butylate / tetrahydrofuran / 0.75 h / -78 °C 8: lithium aluminium tetrahydride / tetrahydrofuran; 1,4-dioxane / 17 h / Reflux View Scheme |
chelidonine
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: triphenylphosphine; carbon tetrabromide / dichloromethane / 0.5 h / 0 - 20 °C 2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 - 20 °C 3: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 1 h / 70 °C / Inert atmosphere 4: N-Bromosuccinimide; water / tetrahydrofuran / 1.5 h / 20 °C 5: potassium tert-butylate / tetrahydrofuran / 0.75 h / -78 °C 6: lithium aluminium tetrahydride / tetrahydrofuran; 1,4-dioxane / 17 h / Reflux View Scheme |
chelidonine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 1 h / 70 °C / Inert atmosphere 2: N-Bromosuccinimide; water / tetrahydrofuran / 1.5 h / 20 °C 3: potassium tert-butylate / tetrahydrofuran / 0.75 h / -78 °C 4: lithium aluminium tetrahydride / tetrahydrofuran; 1,4-dioxane / 17 h / Reflux View Scheme |
chelidonine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; water / tetrahydrofuran / 1.5 h / 20 °C 2: potassium tert-butylate / tetrahydrofuran / 0.75 h / -78 °C 3: lithium aluminium tetrahydride / tetrahydrofuran; 1,4-dioxane / 17 h / Reflux View Scheme |
chelidonine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium tert-butylate / tetrahydrofuran / 0.75 h / -78 °C 2: lithium aluminium tetrahydride / tetrahydrofuran; 1,4-dioxane / 17 h / Reflux View Scheme |
chelidonine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 - 20 °C 2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 1 h / 70 °C / Inert atmosphere 3: N-Bromosuccinimide; water / tetrahydrofuran / 1.5 h / 20 °C 4: potassium tert-butylate / tetrahydrofuran / 0.75 h / -78 °C 5: lithium aluminium tetrahydride / tetrahydrofuran; 1,4-dioxane / 17 h / Reflux View Scheme |
N-t-butyloxycarbonyl-DL-alanine
chelidonine
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; | 95.4% |
Conditions | Yield |
---|---|
With dmap In N,N-dimethyl-formamide at 60℃; for 7h; | 95.1% |
chelidonine
A
(+)-chelidonine N-oxide
B
(+)-chelidonine N-oxide
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In chloroform for 0.666667h; Ambient temperature; | A 14.5% B 83% |
With 3-chloro-benzenecarboperoxoic acid In chloroform for 1h; Ambient temperature; | A 14.5% B 83% |
Conditions | Yield |
---|---|
With pyridine In dichloromethane | 81% |
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; for 10h; | 78.1% |
Conditions | Yield |
---|---|
With pyridine In chloroform at 20℃; | 77.3% |
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; for 3h; | 71.1% |
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; for 5h; | 70.5% |
Conditions | Yield |
---|---|
With pyridine In chloroform | 67.2% |
Conditions | Yield |
---|---|
With pyridine In dichloromethane | 58.1% |
Conditions | Yield |
---|---|
With pyridine In chloroform | 50.8% |
Conditions | Yield |
---|---|
With sodium hydride | 50.4% |
Conditions | Yield |
---|---|
With pyridine In chloroform at 20℃; for 10h; | 50% |
C18H22N2O9S
chelidonine
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; | 47% |
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; | 46% |
4-(2-(2-((3-carboxypropanoyl)oxy)ethoxy)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole-2-oxide
chelidonine
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; | 46% |
chelidonine
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; | 45% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 8h; | 45% |
C17H20N2O9S
chelidonine
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; | 45% |
chelidonine
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; | 44% |
chelidonine
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; | 43% |
chelidonine
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; | 41% |
chelidonine
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; | 38% |
4-(4-((3-carboxypropanoyl)oxy)n-propoxy)-3-benzenesulfonyl-1,2,5-oxadiazole-2-oxide
chelidonine
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; | 38% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 10h; | 38% |
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 60℃; for 10h; | 36.5% |
C16H18N2O9S
chelidonine
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; | 36% |
chelidonine
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; | 35% |
chelidonine
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; | 34% |
chelidonine
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; | 33% |
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