Gossypol Acetate Extract Specification: Name: Gossypol Acetate Extract Identification Standardization Asp
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Product Name: GOSSYPOL Synonyms: 1,1',6,6',7,7'-HEXAHYDROXY-3,3'-DIMETHYL-5,5'-BIS(1-METHYLETHYL)-[2,2'-BINAPHTHALENE]-8,8'-DICARBOXALDEHYDE;2,2'-BIS[8-FORMYL-1
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inquiryAppearance:Brownish-yellow powder Storage:R.T Package:1kg/Bottle or at customers requirement Application:It has an antitumor effect and can be used as a male contraceptive Transportation:Express/Sea/Air Port:Any port in China
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(±)-gossypol acetic acid
(rac)-gossypol
Conditions | Yield |
---|---|
With iron(III) chloride In acetone at 60℃; | 85% |
In diethyl ether; water at 25℃; for 0.166667h; Temperature; Solvent; Sonication; | 105 mg |
2,3,8-trihydroxy-4-isopropyl-6-methyl-1-naphthaldehyde
(rac)-gossypol
Conditions | Yield |
---|---|
With tert-butyl peroxyacetate In 1,2-dichloro-ethane at 80℃; for 4h; Inert atmosphere; | 76.1% |
With tert-butyl peroxyacetate In 1,2-dichloro-ethane at 80℃; for 2.5h; Temperature; Inert atmosphere; | 52% |
With tert-butyl peroxyacetate In 1,2-dichloro-ethane; mineral oil at 80℃; for 2.5h; Inert atmosphere; Schlenk technique; | 41% |
With laccase of Coriolus versicolor; oxygen at 30℃; pH=5.5; aq. phosphate buffer; |
Conditions | Yield |
---|---|
With hydroquinone at 180℃; under 5 - 15 Torr; for 2.5h; | 72% |
apogossypol
(rac)-gossypol
Conditions | Yield |
---|---|
With Dichloromethyl methyl ether; titanium tetrachloride In dichloromethane at 0 - 20℃; for 5h; Inert atmosphere; | 37% |
4,4'-dihydroxy-5,5'-diisopropyl-7,7'-dimethyl-bis(3H-naphtho[1,8-bc]furan-3-one)
(rac)-gossypol
Conditions | Yield |
---|---|
In water; acetone for 48h; |
Gossypol
(rac)-gossypol
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol at 25℃; Kinetics; Mechanism; Thermodynamic data; other temperatures, ΔH(excit.), ΔS(excit.), ΔG(excit.); |
(rac)-gossypol
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid In diethyl ether Heating; |
(rac)-gossypol
Conditions | Yield |
---|---|
With hydrogenchloride; acetic acid In diethyl ether Heating; |
(rac)-gossypol
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: silver(l) oxide / methanol / 3 h / 20 °C 2: potassium carbonate / acetone / 5 h / 20 °C 3: dichloromethane / 0.5 h / 20 °C 4: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 6: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 7: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 7 steps 1: silver(l) oxide / 2 h / Reflux 2: potassium carbonate / acetone / 5 h / 20 °C 3: dichloromethane / 0.5 h / 20 °C 4: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 6: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 7: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 8 steps 1: silver(l) oxide / methanol / 3 h / 20 °C 2: potassium carbonate / acetone / 5 h / 20 °C 3: dichloromethane / 0.5 h / 20 °C 4: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 6: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 7: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 8: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 8 steps 1: silver(l) oxide / 2 h / Reflux 2: potassium carbonate / acetone / 5 h / 20 °C 3: dichloromethane / 0.5 h / 20 °C 4: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 6: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 7: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 8: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme |
(rac)-gossypol
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: potassium carbonate / acetone / 5 h / 20 °C 2: dichloromethane / 0.5 h / 20 °C 3: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 4: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 5: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 6: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 7 steps 1: potassium carbonate / acetone / 5 h / 20 °C 2: dichloromethane / 0.5 h / 20 °C 3: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 4: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 5: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 6: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 7: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme |
(rac)-gossypol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: dichloromethane / 0.5 h / 20 °C 2: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 4: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 5: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 6 steps 1: dichloromethane / 0.5 h / 20 °C 2: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 4: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 5: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 6: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 4 steps 1.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere; Schlenk technique 1.2: 20 °C / Inert atmosphere; Schlenk technique 2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C / Inert atmosphere; Schlenk technique 3.1: boron tribromide / dichloromethane / 10 h / -78 - -10 °C / Inert atmosphere; Schlenk technique 4.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane; mineral oil / 2.5 h / 80 °C / Inert atmosphere; Schlenk technique View Scheme | |
Multi-step reaction with 4 steps 1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 2: 2-Iodobenzoic acid / dimethyl sulfoxide / 12 h 3: boron tribromide / dichloromethane / 10 h / -78 - -10 °C 4: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 2.5 h / 80 °C / Inert atmosphere View Scheme |
(rac)-gossypol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 2: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 3: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 4 steps 1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 2: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 3: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 4: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C / Inert atmosphere; Schlenk technique 2: boron tribromide / dichloromethane / 10 h / -78 - -10 °C / Inert atmosphere; Schlenk technique 3: tert-butyl peroxyacetate / 1,2-dichloro-ethane; mineral oil / 2.5 h / 80 °C / Inert atmosphere; Schlenk technique View Scheme | |
Multi-step reaction with 3 steps 1: 2-Iodobenzoic acid / dimethyl sulfoxide / 12 h 2: boron tribromide / dichloromethane / 10 h / -78 - -10 °C 3: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 2.5 h / 80 °C / Inert atmosphere View Scheme |
4-isopropyl-2,3,8-trimethoxy-6-methyl-1-naphthaldehyde
(rac)-gossypol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 2: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 2: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 3: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: boron tribromide / dichloromethane / 10 h / -78 - -10 °C / Inert atmosphere; Schlenk technique 2: tert-butyl peroxyacetate / 1,2-dichloro-ethane; mineral oil / 2.5 h / 80 °C / Inert atmosphere; Schlenk technique View Scheme | |
Multi-step reaction with 2 steps 1: boron tribromide / dichloromethane / 10 h / -78 - -10 °C 2: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 2.5 h / 80 °C / Inert atmosphere View Scheme |
4-hydroxy-5-isopropyl-7-methylnaphtho[1,8-bc]furan-3-one
(rac)-gossypol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 2: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 17 steps 1.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice 2.1: potassium carbonate / acetone / 15 h / 30 °C 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C 3.2: 2 h / Reflux 4.1: potassium carbonate / acetone / 12 h / 20 °C 5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 5.2: 10 h / -78 - -30 °C / Inert atmosphere 6.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 7.1: acetic anhydride; sodium acetate / 2 h / Reflux 8.1: sodium hydroxide / methanol; water / Reflux 9.1: potassium carbonate / acetone / 12 h / 20 °C 10.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 10.2: 10 h / 20 °C 11.1: silver(l) oxide / methanol / 3 h / 20 °C 12.1: potassium carbonate / acetone / 5 h / 20 °C 13.1: dichloromethane / 0.5 h / 20 °C 14.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 15.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 16.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 17.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 17 steps 1.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice 2.1: potassium carbonate / acetone / 15 h / 30 °C 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C 3.2: 2 h / Reflux 4.1: potassium carbonate / acetone / 12 h / 20 °C 5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 5.2: 10 h / -78 - -30 °C / Inert atmosphere 6.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 7.1: acetic anhydride; sodium acetate / 2 h / Reflux 8.1: sodium hydroxide / methanol; water / Reflux 9.1: potassium carbonate / acetone / 12 h / 20 °C 10.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 10.2: 10 h / 20 °C 11.1: silver(l) oxide / 2 h / Reflux 12.1: potassium carbonate / acetone / 5 h / 20 °C 13.1: dichloromethane / 0.5 h / 20 °C 14.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 15.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 16.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 17.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 18 steps 1.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice 2.1: potassium carbonate / acetone / 15 h / 30 °C 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C 3.2: 2 h / Reflux 4.1: potassium carbonate / acetone / 12 h / 20 °C 5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 5.2: 10 h / -78 - -30 °C / Inert atmosphere 6.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 7.1: acetic anhydride; sodium acetate / 2 h / Reflux 8.1: sodium hydroxide / methanol; water / Reflux 9.1: potassium carbonate / acetone / 12 h / 20 °C 10.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 10.2: 10 h / 20 °C 11.1: silver(l) oxide / methanol / 3 h / 20 °C 12.1: potassium carbonate / acetone / 5 h / 20 °C 13.1: dichloromethane / 0.5 h / 20 °C 14.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 15.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 16.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 17.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 18.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 18 steps 1.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice 2.1: potassium carbonate / acetone / 15 h / 30 °C 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C 3.2: 2 h / Reflux 4.1: potassium carbonate / acetone / 12 h / 20 °C 5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 5.2: 10 h / -78 - -30 °C / Inert atmosphere 6.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 7.1: acetic anhydride; sodium acetate / 2 h / Reflux 8.1: sodium hydroxide / methanol; water / Reflux 9.1: potassium carbonate / acetone / 12 h / 20 °C 10.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 10.2: 10 h / 20 °C 11.1: silver(l) oxide / 2 h / Reflux 12.1: potassium carbonate / acetone / 5 h / 20 °C 13.1: dichloromethane / 0.5 h / 20 °C 14.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 15.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 16.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 17.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 18.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 18 steps 1.1: tin(IV) chloride; triethylamine / toluene / 0.33 h / 20 °C / Inert atmosphere 1.2: 8 h / 100 °C / Inert atmosphere 2.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice 3.1: potassium carbonate / acetone / 15 h / 30 °C 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C 4.2: 2 h / Reflux 5.1: potassium carbonate / acetone / 12 h / 20 °C 6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 6.2: 10 h / -78 - -30 °C / Inert atmosphere 7.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 8.1: acetic anhydride; sodium acetate / 2 h / Reflux 9.1: sodium hydroxide / methanol; water / Reflux 10.1: potassium carbonate / acetone / 12 h / 20 °C 11.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 11.2: 10 h / 20 °C 12.1: silver(l) oxide / methanol / 3 h / 20 °C 13.1: potassium carbonate / acetone / 5 h / 20 °C 14.1: dichloromethane / 0.5 h / 20 °C 15.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 16.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 17.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 18.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 18 steps 1.1: tin(IV) chloride; triethylamine / toluene / 0.33 h / 20 °C / Inert atmosphere 1.2: 8 h / 100 °C / Inert atmosphere 2.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice 3.1: potassium carbonate / acetone / 15 h / 30 °C 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C 4.2: 2 h / Reflux 5.1: potassium carbonate / acetone / 12 h / 20 °C 6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 6.2: 10 h / -78 - -30 °C / Inert atmosphere 7.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 8.1: acetic anhydride; sodium acetate / 2 h / Reflux 9.1: sodium hydroxide / methanol; water / Reflux 10.1: potassium carbonate / acetone / 12 h / 20 °C 11.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 11.2: 10 h / 20 °C 12.1: silver(l) oxide / 2 h / Reflux 13.1: potassium carbonate / acetone / 5 h / 20 °C 14.1: dichloromethane / 0.5 h / 20 °C 15.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 16.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 17.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 18.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 19 steps 1.1: tin(IV) chloride; triethylamine / toluene / 0.33 h / 20 °C / Inert atmosphere 1.2: 8 h / 100 °C / Inert atmosphere 2.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice 3.1: potassium carbonate / acetone / 15 h / 30 °C 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C 4.2: 2 h / Reflux 5.1: potassium carbonate / acetone / 12 h / 20 °C 6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 6.2: 10 h / -78 - -30 °C / Inert atmosphere 7.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 8.1: acetic anhydride; sodium acetate / 2 h / Reflux 9.1: sodium hydroxide / methanol; water / Reflux 10.1: potassium carbonate / acetone / 12 h / 20 °C 11.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 11.2: 10 h / 20 °C 12.1: silver(l) oxide / methanol / 3 h / 20 °C 13.1: potassium carbonate / acetone / 5 h / 20 °C 14.1: dichloromethane / 0.5 h / 20 °C 15.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 16.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 17.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 18.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 19.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 19 steps 1.1: tin(IV) chloride; triethylamine / toluene / 0.33 h / 20 °C / Inert atmosphere 1.2: 8 h / 100 °C / Inert atmosphere 2.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice 3.1: potassium carbonate / acetone / 15 h / 30 °C 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C 4.2: 2 h / Reflux 5.1: potassium carbonate / acetone / 12 h / 20 °C 6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 6.2: 10 h / -78 - -30 °C / Inert atmosphere 7.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 8.1: acetic anhydride; sodium acetate / 2 h / Reflux 9.1: sodium hydroxide / methanol; water / Reflux 10.1: potassium carbonate / acetone / 12 h / 20 °C 11.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 11.2: 10 h / 20 °C 12.1: silver(l) oxide / 2 h / Reflux 13.1: potassium carbonate / acetone / 5 h / 20 °C 14.1: dichloromethane / 0.5 h / 20 °C 15.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 16.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 17.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 18.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 19.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme |
(rac)-gossypol
Conditions | Yield |
---|---|
Multi-step reaction with 16 steps 1.1: potassium carbonate / acetone / 15 h / 30 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C 2.2: 2 h / Reflux 3.1: potassium carbonate / acetone / 12 h / 20 °C 4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 4.2: 10 h / -78 - -30 °C / Inert atmosphere 5.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 6.1: acetic anhydride; sodium acetate / 2 h / Reflux 7.1: sodium hydroxide / methanol; water / Reflux 8.1: potassium carbonate / acetone / 12 h / 20 °C 9.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 9.2: 10 h / 20 °C 10.1: silver(l) oxide / methanol / 3 h / 20 °C 11.1: potassium carbonate / acetone / 5 h / 20 °C 12.1: dichloromethane / 0.5 h / 20 °C 13.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 14.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 15.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 16.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 16 steps 1.1: potassium carbonate / acetone / 15 h / 30 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C 2.2: 2 h / Reflux 3.1: potassium carbonate / acetone / 12 h / 20 °C 4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 4.2: 10 h / -78 - -30 °C / Inert atmosphere 5.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 6.1: acetic anhydride; sodium acetate / 2 h / Reflux 7.1: sodium hydroxide / methanol; water / Reflux 8.1: potassium carbonate / acetone / 12 h / 20 °C 9.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 9.2: 10 h / 20 °C 10.1: silver(l) oxide / 2 h / Reflux 11.1: potassium carbonate / acetone / 5 h / 20 °C 12.1: dichloromethane / 0.5 h / 20 °C 13.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 14.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 15.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 16.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 17 steps 1.1: potassium carbonate / acetone / 15 h / 30 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C 2.2: 2 h / Reflux 3.1: potassium carbonate / acetone / 12 h / 20 °C 4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 4.2: 10 h / -78 - -30 °C / Inert atmosphere 5.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 6.1: acetic anhydride; sodium acetate / 2 h / Reflux 7.1: sodium hydroxide / methanol; water / Reflux 8.1: potassium carbonate / acetone / 12 h / 20 °C 9.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 9.2: 10 h / 20 °C 10.1: silver(l) oxide / methanol / 3 h / 20 °C 11.1: potassium carbonate / acetone / 5 h / 20 °C 12.1: dichloromethane / 0.5 h / 20 °C 13.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 14.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 15.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 16.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 17.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 17 steps 1.1: potassium carbonate / acetone / 15 h / 30 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C 2.2: 2 h / Reflux 3.1: potassium carbonate / acetone / 12 h / 20 °C 4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 4.2: 10 h / -78 - -30 °C / Inert atmosphere 5.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 6.1: acetic anhydride; sodium acetate / 2 h / Reflux 7.1: sodium hydroxide / methanol; water / Reflux 8.1: potassium carbonate / acetone / 12 h / 20 °C 9.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 9.2: 10 h / 20 °C 10.1: silver(l) oxide / 2 h / Reflux 11.1: potassium carbonate / acetone / 5 h / 20 °C 12.1: dichloromethane / 0.5 h / 20 °C 13.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 14.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 15.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 16.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 17.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme |
(rac)-gossypol
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: potassium carbonate / acetone / 12 h / 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 2.2: 10 h / 20 °C 3.1: silver(l) oxide / methanol / 3 h / 20 °C 4.1: potassium carbonate / acetone / 5 h / 20 °C 5.1: dichloromethane / 0.5 h / 20 °C 6.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 8.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 9.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 10.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 10 steps 1.1: potassium carbonate / acetone / 12 h / 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 2.2: 10 h / 20 °C 3.1: silver(l) oxide / 2 h / Reflux 4.1: potassium carbonate / acetone / 5 h / 20 °C 5.1: dichloromethane / 0.5 h / 20 °C 6.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 8.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 9.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 10.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 9 steps 1.1: potassium carbonate / acetone / 12 h / 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 2.2: 10 h / 20 °C 3.1: silver(l) oxide / 2 h / Reflux 4.1: potassium carbonate / acetone / 5 h / 20 °C 5.1: dichloromethane / 0.5 h / 20 °C 6.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 8.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 9.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 9 steps 1.1: potassium carbonate / acetone / 12 h / 20 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 2.2: 10 h / 20 °C 3.1: silver(l) oxide / methanol / 3 h / 20 °C 4.1: potassium carbonate / acetone / 5 h / 20 °C 5.1: dichloromethane / 0.5 h / 20 °C 6.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 8.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 9.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme |
(rac)-gossypol
Conditions | Yield |
---|---|
Multi-step reaction with 15 steps 1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C 1.2: 2 h / Reflux 2.1: potassium carbonate / acetone / 12 h / 20 °C 3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 3.2: 10 h / -78 - -30 °C / Inert atmosphere 4.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 5.1: acetic anhydride; sodium acetate / 2 h / Reflux 6.1: sodium hydroxide / methanol; water / Reflux 7.1: potassium carbonate / acetone / 12 h / 20 °C 8.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 8.2: 10 h / 20 °C 9.1: silver(l) oxide / methanol / 3 h / 20 °C 10.1: potassium carbonate / acetone / 5 h / 20 °C 11.1: dichloromethane / 0.5 h / 20 °C 12.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 13.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 14.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 15.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 15 steps 1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C 1.2: 2 h / Reflux 2.1: potassium carbonate / acetone / 12 h / 20 °C 3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 3.2: 10 h / -78 - -30 °C / Inert atmosphere 4.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 5.1: acetic anhydride; sodium acetate / 2 h / Reflux 6.1: sodium hydroxide / methanol; water / Reflux 7.1: potassium carbonate / acetone / 12 h / 20 °C 8.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 8.2: 10 h / 20 °C 9.1: silver(l) oxide / 2 h / Reflux 10.1: potassium carbonate / acetone / 5 h / 20 °C 11.1: dichloromethane / 0.5 h / 20 °C 12.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 13.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 14.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 15.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 16 steps 1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C 1.2: 2 h / Reflux 2.1: potassium carbonate / acetone / 12 h / 20 °C 3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 3.2: 10 h / -78 - -30 °C / Inert atmosphere 4.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 5.1: acetic anhydride; sodium acetate / 2 h / Reflux 6.1: sodium hydroxide / methanol; water / Reflux 7.1: potassium carbonate / acetone / 12 h / 20 °C 8.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 8.2: 10 h / 20 °C 9.1: silver(l) oxide / methanol / 3 h / 20 °C 10.1: potassium carbonate / acetone / 5 h / 20 °C 11.1: dichloromethane / 0.5 h / 20 °C 12.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 13.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 14.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 15.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 16.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 16 steps 1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C 1.2: 2 h / Reflux 2.1: potassium carbonate / acetone / 12 h / 20 °C 3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 3.2: 10 h / -78 - -30 °C / Inert atmosphere 4.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 5.1: acetic anhydride; sodium acetate / 2 h / Reflux 6.1: sodium hydroxide / methanol; water / Reflux 7.1: potassium carbonate / acetone / 12 h / 20 °C 8.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 8.2: 10 h / 20 °C 9.1: silver(l) oxide / 2 h / Reflux 10.1: potassium carbonate / acetone / 5 h / 20 °C 11.1: dichloromethane / 0.5 h / 20 °C 12.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 13.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 14.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 15.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 16.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme |
(rac)-gossypol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 3: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 4: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 5 steps 1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 3: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 4: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 5: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme |
(rac)-gossypol
Conditions | Yield |
---|---|
Multi-step reaction with 14 steps 1.1: potassium carbonate / acetone / 12 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 10 h / -78 - -30 °C / Inert atmosphere 3.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 4.1: acetic anhydride; sodium acetate / 2 h / Reflux 5.1: sodium hydroxide / methanol; water / Reflux 6.1: potassium carbonate / acetone / 12 h / 20 °C 7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 7.2: 10 h / 20 °C 8.1: silver(l) oxide / methanol / 3 h / 20 °C 9.1: potassium carbonate / acetone / 5 h / 20 °C 10.1: dichloromethane / 0.5 h / 20 °C 11.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 12.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 13.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 14.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 14 steps 1.1: potassium carbonate / acetone / 12 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 10 h / -78 - -30 °C / Inert atmosphere 3.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 4.1: acetic anhydride; sodium acetate / 2 h / Reflux 5.1: sodium hydroxide / methanol; water / Reflux 6.1: potassium carbonate / acetone / 12 h / 20 °C 7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 7.2: 10 h / 20 °C 8.1: silver(l) oxide / 2 h / Reflux 9.1: potassium carbonate / acetone / 5 h / 20 °C 10.1: dichloromethane / 0.5 h / 20 °C 11.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 12.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 13.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 14.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 15 steps 1.1: potassium carbonate / acetone / 12 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 10 h / -78 - -30 °C / Inert atmosphere 3.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 4.1: acetic anhydride; sodium acetate / 2 h / Reflux 5.1: sodium hydroxide / methanol; water / Reflux 6.1: potassium carbonate / acetone / 12 h / 20 °C 7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 7.2: 10 h / 20 °C 8.1: silver(l) oxide / methanol / 3 h / 20 °C 9.1: potassium carbonate / acetone / 5 h / 20 °C 10.1: dichloromethane / 0.5 h / 20 °C 11.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 12.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 13.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 14.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 15.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 15 steps 1.1: potassium carbonate / acetone / 12 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 10 h / -78 - -30 °C / Inert atmosphere 3.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 4.1: acetic anhydride; sodium acetate / 2 h / Reflux 5.1: sodium hydroxide / methanol; water / Reflux 6.1: potassium carbonate / acetone / 12 h / 20 °C 7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 7.2: 10 h / 20 °C 8.1: silver(l) oxide / 2 h / Reflux 9.1: potassium carbonate / acetone / 5 h / 20 °C 10.1: dichloromethane / 0.5 h / 20 °C 11.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 12.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 13.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 14.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 15.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme |
(rac)-gossypol
Conditions | Yield |
---|---|
Multi-step reaction with 13 steps 1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 10 h / -78 - -30 °C / Inert atmosphere 2.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 3.1: acetic anhydride; sodium acetate / 2 h / Reflux 4.1: sodium hydroxide / methanol; water / Reflux 5.1: potassium carbonate / acetone / 12 h / 20 °C 6.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 6.2: 10 h / 20 °C 7.1: silver(l) oxide / methanol / 3 h / 20 °C 8.1: potassium carbonate / acetone / 5 h / 20 °C 9.1: dichloromethane / 0.5 h / 20 °C 10.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 11.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 12.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 13.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 13 steps 1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 10 h / -78 - -30 °C / Inert atmosphere 2.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 3.1: acetic anhydride; sodium acetate / 2 h / Reflux 4.1: sodium hydroxide / methanol; water / Reflux 5.1: potassium carbonate / acetone / 12 h / 20 °C 6.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 6.2: 10 h / 20 °C 7.1: silver(l) oxide / 2 h / Reflux 8.1: potassium carbonate / acetone / 5 h / 20 °C 9.1: dichloromethane / 0.5 h / 20 °C 10.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 11.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 12.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 13.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 14 steps 1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 10 h / -78 - -30 °C / Inert atmosphere 2.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 3.1: acetic anhydride; sodium acetate / 2 h / Reflux 4.1: sodium hydroxide / methanol; water / Reflux 5.1: potassium carbonate / acetone / 12 h / 20 °C 6.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 6.2: 10 h / 20 °C 7.1: silver(l) oxide / methanol / 3 h / 20 °C 8.1: potassium carbonate / acetone / 5 h / 20 °C 9.1: dichloromethane / 0.5 h / 20 °C 10.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 11.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 12.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 13.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 14.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 14 steps 1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 10 h / -78 - -30 °C / Inert atmosphere 2.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 3.1: acetic anhydride; sodium acetate / 2 h / Reflux 4.1: sodium hydroxide / methanol; water / Reflux 5.1: potassium carbonate / acetone / 12 h / 20 °C 6.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 6.2: 10 h / 20 °C 7.1: silver(l) oxide / 2 h / Reflux 8.1: potassium carbonate / acetone / 5 h / 20 °C 9.1: dichloromethane / 0.5 h / 20 °C 10.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 11.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 12.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 13.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 14.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme |
(rac)-gossypol
Conditions | Yield |
---|---|
Multi-step reaction with 12 steps 1.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 2.1: acetic anhydride; sodium acetate / 2 h / Reflux 3.1: sodium hydroxide / methanol; water / Reflux 4.1: potassium carbonate / acetone / 12 h / 20 °C 5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 5.2: 10 h / 20 °C 6.1: silver(l) oxide / methanol / 3 h / 20 °C 7.1: potassium carbonate / acetone / 5 h / 20 °C 8.1: dichloromethane / 0.5 h / 20 °C 9.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 11.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 12.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 12 steps 1.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 2.1: acetic anhydride; sodium acetate / 2 h / Reflux 3.1: sodium hydroxide / methanol; water / Reflux 4.1: potassium carbonate / acetone / 12 h / 20 °C 5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 5.2: 10 h / 20 °C 6.1: silver(l) oxide / 2 h / Reflux 7.1: potassium carbonate / acetone / 5 h / 20 °C 8.1: dichloromethane / 0.5 h / 20 °C 9.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 11.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 12.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 13 steps 1.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 2.1: acetic anhydride; sodium acetate / 2 h / Reflux 3.1: sodium hydroxide / methanol; water / Reflux 4.1: potassium carbonate / acetone / 12 h / 20 °C 5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 5.2: 10 h / 20 °C 6.1: silver(l) oxide / methanol / 3 h / 20 °C 7.1: potassium carbonate / acetone / 5 h / 20 °C 8.1: dichloromethane / 0.5 h / 20 °C 9.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 11.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 12.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 13.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 13 steps 1.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C 2.1: acetic anhydride; sodium acetate / 2 h / Reflux 3.1: sodium hydroxide / methanol; water / Reflux 4.1: potassium carbonate / acetone / 12 h / 20 °C 5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 5.2: 10 h / 20 °C 6.1: silver(l) oxide / 2 h / Reflux 7.1: potassium carbonate / acetone / 5 h / 20 °C 8.1: dichloromethane / 0.5 h / 20 °C 9.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 11.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 12.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 13.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme |
(rac)-gossypol
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1.1: acetic anhydride; sodium acetate / 2 h / Reflux 2.1: sodium hydroxide / methanol; water / Reflux 3.1: potassium carbonate / acetone / 12 h / 20 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 4.2: 10 h / 20 °C 5.1: silver(l) oxide / methanol / 3 h / 20 °C 6.1: potassium carbonate / acetone / 5 h / 20 °C 7.1: dichloromethane / 0.5 h / 20 °C 8.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 9.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 10.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 11.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 11 steps 1.1: acetic anhydride; sodium acetate / 2 h / Reflux 2.1: sodium hydroxide / methanol; water / Reflux 3.1: potassium carbonate / acetone / 12 h / 20 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 4.2: 10 h / 20 °C 5.1: silver(l) oxide / 2 h / Reflux 6.1: potassium carbonate / acetone / 5 h / 20 °C 7.1: dichloromethane / 0.5 h / 20 °C 8.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 9.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 10.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 11.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 12 steps 1.1: acetic anhydride; sodium acetate / 2 h / Reflux 2.1: sodium hydroxide / methanol; water / Reflux 3.1: potassium carbonate / acetone / 12 h / 20 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 4.2: 10 h / 20 °C 5.1: silver(l) oxide / methanol / 3 h / 20 °C 6.1: potassium carbonate / acetone / 5 h / 20 °C 7.1: dichloromethane / 0.5 h / 20 °C 8.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 9.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 10.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 11.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 12.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 12 steps 1.1: acetic anhydride; sodium acetate / 2 h / Reflux 2.1: sodium hydroxide / methanol; water / Reflux 3.1: potassium carbonate / acetone / 12 h / 20 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 4.2: 10 h / 20 °C 5.1: silver(l) oxide / 2 h / Reflux 6.1: potassium carbonate / acetone / 5 h / 20 °C 7.1: dichloromethane / 0.5 h / 20 °C 8.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 9.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 10.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 11.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 12.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme |
(rac)-gossypol
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: sodium hydroxide / methanol; water / Reflux 2.1: potassium carbonate / acetone / 12 h / 20 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 3.2: 10 h / 20 °C 4.1: silver(l) oxide / methanol / 3 h / 20 °C 5.1: potassium carbonate / acetone / 5 h / 20 °C 6.1: dichloromethane / 0.5 h / 20 °C 7.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 9.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 10.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 10 steps 1.1: sodium hydroxide / methanol; water / Reflux 2.1: potassium carbonate / acetone / 12 h / 20 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 3.2: 10 h / 20 °C 4.1: silver(l) oxide / 2 h / Reflux 5.1: potassium carbonate / acetone / 5 h / 20 °C 6.1: dichloromethane / 0.5 h / 20 °C 7.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 9.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 10.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 11 steps 1.1: sodium hydroxide / methanol; water / Reflux 2.1: potassium carbonate / acetone / 12 h / 20 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 3.2: 10 h / 20 °C 4.1: silver(l) oxide / methanol / 3 h / 20 °C 5.1: potassium carbonate / acetone / 5 h / 20 °C 6.1: dichloromethane / 0.5 h / 20 °C 7.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 9.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 10.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 11.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 11 steps 1.1: sodium hydroxide / methanol; water / Reflux 2.1: potassium carbonate / acetone / 12 h / 20 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 3.2: 10 h / 20 °C 4.1: silver(l) oxide / 2 h / Reflux 5.1: potassium carbonate / acetone / 5 h / 20 °C 6.1: dichloromethane / 0.5 h / 20 °C 7.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 9.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 10.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 11.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme |
(rac)-gossypol
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 1.2: 10 h / 20 °C 2.1: silver(l) oxide / 2 h / Reflux 3.1: potassium carbonate / acetone / 5 h / 20 °C 4.1: dichloromethane / 0.5 h / 20 °C 5.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 7.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 8.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 8 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 1.2: 10 h / 20 °C 2.1: silver(l) oxide / methanol / 3 h / 20 °C 3.1: potassium carbonate / acetone / 5 h / 20 °C 4.1: dichloromethane / 0.5 h / 20 °C 5.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 7.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 8.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 9 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 1.2: 10 h / 20 °C 2.1: silver(l) oxide / 2 h / Reflux 3.1: potassium carbonate / acetone / 5 h / 20 °C 4.1: dichloromethane / 0.5 h / 20 °C 5.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 7.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 8.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 9.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 9 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 1.2: 10 h / 20 °C 2.1: silver(l) oxide / methanol / 3 h / 20 °C 3.1: potassium carbonate / acetone / 5 h / 20 °C 4.1: dichloromethane / 0.5 h / 20 °C 5.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C 6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C 7.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere 8.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C 9.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere View Scheme |
(rac)-gossypol
Conditions | Yield |
---|---|
Multi-step reaction with 13 steps 1.1: sodium tetrahydroborate; methanol / 0.5 h / 0 °C / Inert atmosphere; Schlenk technique 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.75 h / 0 °C / Inert atmosphere; Schlenk technique 2.2: 14 h / 0 - 20 °C / Inert atmosphere; Schlenk technique 3.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 32 h / 20 °C / Schlenk technique 4.1: potassium tert-butylate / tetrahydrofuran / 0.75 h / 0 - 20 °C / Inert atmosphere; Schlenk technique 4.2: 2 h / 20 °C / Inert atmosphere; Schlenk technique 5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 4 h / 20 °C / Inert atmosphere; Schlenk technique 6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C / Inert atmosphere; Schlenk technique 7.1: 2,6-di-tert-butyl-4-methyl-phenol / chlorobenzene / 13 h / 160 °C / Schlenk technique; Inert atmosphere 8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C / Inert atmosphere; Schlenk technique 9.1: potassium carbonate / acetonitrile / 20 h / 80 °C / Inert atmosphere; Schlenk technique 10.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere; Schlenk technique 10.2: 20 °C / Inert atmosphere; Schlenk technique 11.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C / Inert atmosphere; Schlenk technique 12.1: boron tribromide / dichloromethane / 10 h / -78 - -10 °C / Inert atmosphere; Schlenk technique 13.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane; mineral oil / 2.5 h / 80 °C / Inert atmosphere; Schlenk technique View Scheme |
(rac)-gossypol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: potassium carbonate / acetonitrile / 20 h / 80 °C / Inert atmosphere; Schlenk technique 2.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere; Schlenk technique 2.2: 20 °C / Inert atmosphere; Schlenk technique 3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C / Inert atmosphere; Schlenk technique 4.1: boron tribromide / dichloromethane / 10 h / -78 - -10 °C / Inert atmosphere; Schlenk technique 5.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane; mineral oil / 2.5 h / 80 °C / Inert atmosphere; Schlenk technique View Scheme | |
Multi-step reaction with 5 steps 1: potassium carbonate / acetonitrile / 4 h / 80 °C 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 3: 2-Iodobenzoic acid / dimethyl sulfoxide / 12 h 4: boron tribromide / dichloromethane / 10 h / -78 - -10 °C 5: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 2.5 h / 80 °C / Inert atmosphere View Scheme |
Conditions | Yield |
---|---|
In methanol for 5h; Ambient temperature; | 100% |
(rac)-gossypol
methyl tryptophanate hydrochloride
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol at 45℃; for 2h; Resolution of racemate; | A 99.4% B 95% |
Conditions | Yield |
---|---|
With acid In ethanol for 3h; Heating; | 98.7% |
Conditions | Yield |
---|---|
at 20℃; | 98% |
(rac)-gossypol
(R)-(+)-tryptophan methyl ester hydrochloride
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol Reflux; | 98% |
(rac)-gossypol
(S)-tryptophan methyl ester hydrochloride
C54H54N4O10
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol Reflux; | 98% |
(rac)-gossypol
(S)-tryptophan methyl ester hydrochloride
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol at 20℃; for 0.5h; | A 97% B 94% |
(rac)-gossypol
ethylamine
1,6,7,1',6',7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthyl-8,8'-dicarbaldehyde bis-ethylimine
Conditions | Yield |
---|---|
In diethyl ether; isopropyl alcohol at 20 - 45℃; for 2.08333h; Condensation; | 96% |
With isopropyl alcohol |
Conditions | Yield |
---|---|
In diethyl ether; isopropyl alcohol at 20 - 45℃; for 2.08333h; Condensation; | 96% |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol for 3h; Heating; | 95.8% |
Conditions | Yield |
---|---|
In ethanol for 3h; Heating; | 95.31% |
(rac)-gossypol
apogossypol
Conditions | Yield |
---|---|
Stage #1: (rac)-gossypol With sodium hydroxide; acetic acid In water at 90℃; for 3.5h; darkness; Stage #2: With sulfuric acid In water at 0℃; | 95% |
Stage #1: (rac)-gossypol With water; sodium hydroxide at 90℃; for 3.5h; Inert atmosphere; Darkness; Stage #2: With sulfuric acid In water Cooling with ice; | 95% |
Stage #1: (rac)-gossypol With sodium hydroxide In water at 90℃; for 3.5h; Inert atmosphere; Darkness; Stage #2: With sulfuric acid In water | 95% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide Condensation; | 95% |
(rac)-gossypol
4-hydroxynon-2-enal
Conditions | Yield |
---|---|
With zinc(II) chloride In acetonitrile at 60℃; for 5h; Reagent/catalyst; Solvent; Temperature; | 93.5% |
Conditions | Yield |
---|---|
Stage #1: 1.3-propanedithiol; (rac)-gossypol In chloroform at 20℃; for 1h; Stage #2: With boron trifluoride diethyl etherate In chloroform at 20℃; for 15h; | 93% |
Conditions | Yield |
---|---|
In methanol at 20℃; for 3h; Inert atmosphere; | 92.9% |
(rac)-gossypol
tetra-acetyl glucosamine
Conditions | Yield |
---|---|
In methanol at 20℃; for 3h; Inert atmosphere; | 92.6% |
Conditions | Yield |
---|---|
With acid In ethanol for 3h; Heating; | 92.3% |
Conditions | Yield |
---|---|
In diethyl ether; isopropyl alcohol at 20 - 45℃; for 2.08333h; Condensation; | 92% |
Conditions | Yield |
---|---|
In diethyl ether; isopropyl alcohol at 20 - 45℃; for 2.08333h; Condensation; | 92% |
Conditions | Yield |
---|---|
In ethanol for 3h; Heating; | 91.9% |
(rac)-gossypol
N-Aminoanabasine
5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-{[(Z)-3,4,5,6-tetrahydro-2H-[2,3']bipyridinyl-1-ylimino]-methyl}-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol
Conditions | Yield |
---|---|
In ethanol Heating; | 91% |
n-Dodecylamine
(rac)-gossypol
1,6,7,1',6',7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthyl-8,8'-dicarbaldehyde bis-dodecylimine
Conditions | Yield |
---|---|
In diethyl ether; isopropyl alcohol at 20 - 45℃; for 2.08333h; Condensation; | 91% |
Conditions | Yield |
---|---|
Stage #1: (rac)-gossypol With iron(III) chloride; acetic acid In water; acetone at 100℃; for 2h; Stage #2: With sulfuric acid In diethyl ether; water | 91% |
With iron(III) chloride In acetic acid; acetone at 60 - 70℃; Oxidation; | 49% |
With iron(III) chloride; acetic acid In acetone at 70℃; for 0.75h; |
Conditions | Yield |
---|---|
With sodium hydroxide In methanol at 20℃; for 3h; pH=7.4; Inert atmosphere; | 90.8% |
Conditions | Yield |
---|---|
In ethanol for 3h; Heating; | 90.17% |
4'-aminobenzo-15-crown-5-ether
(rac)-gossypol
Conditions | Yield |
---|---|
In ethanol for 6h; Heating; | 90.1% |
4-(3-Aminopropyl)morpholine
(rac)-gossypol
5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-{[(Z)-3-morpholin-4-yl-propylimino]-methyl}-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol
Conditions | Yield |
---|---|
In isopropyl alcohol Heating; | 90% |
Conditions | Yield |
---|---|
In diethyl ether; isopropyl alcohol at 20 - 45℃; for 2.08333h; Condensation; | 90% |
Conditions | Yield |
---|---|
In diethyl ether; isopropyl alcohol at 20 - 45℃; for 2.08333h; Condensation; | 90% |
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