69866-21-3

Usage

Safety Profile

Deadly poison by intravenous andintraperitoneal routes. Mutation data reported. Whenheated to decomposition it emits toxic fumes of NOx.

InChI:InChI=1/C37H33N7O8/c1-14-12-39-27-22(45)10-23-37(24(14)27)11-15(37)13-44(23)35(49)21-9-18-16-4-6-42(28(16)30(46)32(51-2)25(18)41-21)34(48)20-8-19-17-5-7-43(36(38)50)29(17)31(47)33(52-3)26(19)40-20/h8-10,12,15,39-41,46-47H,4-7,11,13H2,1-3H3,(H2,38,50)

Synthetic route

C37H34ClN7O8 (112764-71-3) → CC-1065 (69866-21-3)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 4h; Ambient temperature;	45%
With triethylamine In water; acetonitrile at 22℃; for 0.5h;	43%
With triethylamine In water; acetonitrile at 23℃; for 0.5h; Yield given;
With triethylamine In water; acetonitrile for 1h; Ambient temperature; Yield given;

tert-butyl-(1S)-1-(chloromethyl)-5-hydroxy-8-methyl-1,6-dihydropyrrolo[3,2-e]indole-3(2H)-carboxylate (110314-51-7) → CC-1065 (69866-21-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 3M HCl / ethyl acetate / 1 h / Ambient temperature 2: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature 3: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 2: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 3: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme
Multi-step reaction with 3 steps 1: 3N HCl / ethyl acetate / 0.75 h / 23 °C 2: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C 3: Et3N / H2O; acetonitrile / 0.5 h / 23 °C View Scheme
Multi-step reaction with 3 steps 1: hydrogen chloride gas / ethyl acetate / 0.67 h 2: 54 percent / EDC / N,N-dimethyl-acetamide / 2 h / Ambient temperature 3: triethylamine / acetonitrile; H2O / 1 h / Ambient temperature View Scheme

(S)-1,6-dihydro-1-(hydroxymethyl)-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester (112836-67-6) → CC-1065 (69866-21-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: 82 percent / PPh3, CCl4 / CH2Cl2 / 7 h / Ambient temperature 2: 88 percent / 25percent HCO2NH4 / 10percentPd-C / tetrahydrofuran / 6 h / 0 °C 3: 3M HCl / ethyl acetate / 1 h / Ambient temperature 4: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature 5: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature View Scheme
Multi-step reaction with 5 steps 1: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 2: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 3: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 4: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 5: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme
Multi-step reaction with 5 steps 1: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C 2: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C 3: 3N HCl / ethyl acetate / 0.75 h / 23 °C 4: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C 5: Et3N / H2O; acetonitrile / 0.5 h / 23 °C View Scheme
Multi-step reaction with 6 steps 1: pyridine / 6 h / Ambient temperature 2: lithium chloride / dimethylformamide / 0.42 h / 80 °C 3: ammonium formate / 10percent Pd/C / tetrahydrofuran; methanol / 0.33 h / Ambient temperature 4: hydrogen chloride gas / ethyl acetate / 0.67 h 5: 54 percent / EDC / N,N-dimethyl-acetamide / 2 h / Ambient temperature 6: triethylamine / acetonitrile; H2O / 1 h / Ambient temperature View Scheme

(S)-1-(chloromethyl)-1,6-dihydro-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester (110314-50-6) → CC-1065 (69866-21-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 88 percent / 25percent HCO2NH4 / 10percentPd-C / tetrahydrofuran / 6 h / 0 °C 2: 3M HCl / ethyl acetate / 1 h / Ambient temperature 3: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature 4: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature View Scheme
Multi-step reaction with 4 steps 1: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 2: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 3: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 4: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme
Multi-step reaction with 4 steps 1: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C 2: 3N HCl / ethyl acetate / 0.75 h / 23 °C 3: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C 4: Et3N / H2O; acetonitrile / 0.5 h / 23 °C View Scheme
Multi-step reaction with 4 steps 1: ammonium formate / 10percent Pd/C / tetrahydrofuran; methanol / 0.33 h / Ambient temperature 2: hydrogen chloride gas / ethyl acetate / 0.67 h 3: 54 percent / EDC / N,N-dimethyl-acetamide / 2 h / Ambient temperature 4: triethylamine / acetonitrile; H2O / 1 h / Ambient temperature View Scheme

(S)-1-(chloromethyl)-1,6-dihydro-5-hydroxy-8-methylbenzo[1,2-b:4,3-b']dipyrrole hydrochloride (110314-54-0) → CC-1065 (69866-21-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature 2: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 2: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme
Multi-step reaction with 2 steps 1: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C 2: Et3N / H2O; acetonitrile / 0.5 h / 23 °C View Scheme
Multi-step reaction with 2 steps 1: 54 percent / EDC / N,N-dimethyl-acetamide / 2 h / Ambient temperature 2: triethylamine / acetonitrile; H2O / 1 h / Ambient temperature View Scheme

(3S)-3-acetoxymethyl-5-amino-6-benzyloxy-1-(t-butoxycarbonyl)-2,3-dihydroindole → CC-1065 (69866-21-3)

Conditions

Yield

Multi-step reaction with 8 steps 1: 96 percent / methanol / 0 deg C - r.t., overnight 2: 23 percent / Pd(OAc)2 / N,N-dimethyl-acetamide / 70 °C 3: 48 percent / Me2SBH3 / tetrahydrofuran / 19 h / Heating 4: 82 percent / PPh3, CCl4 / CH2Cl2 / 7 h / Ambient temperature 5: 88 percent / 25percent HCO2NH4 / 10percentPd-C / tetrahydrofuran / 6 h / 0 °C 6: 3M HCl / ethyl acetate / 1 h / Ambient temperature 7: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature 8: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature View Scheme

(S)-8-Acetoxymethyl-4-benzyloxy-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1,6-dicarboxylic acid 6-tert-butyl ester 1-methyl ester (176685-39-5) → CC-1065 (69866-21-3)

Conditions

Yield

Multi-step reaction with 6 steps 1: 48 percent / Me2SBH3 / tetrahydrofuran / 19 h / Heating 2: 82 percent / PPh3, CCl4 / CH2Cl2 / 7 h / Ambient temperature 3: 88 percent / 25percent HCO2NH4 / 10percentPd-C / tetrahydrofuran / 6 h / 0 °C 4: 3M HCl / ethyl acetate / 1 h / Ambient temperature 5: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature 6: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature View Scheme

(S)-3-Acetoxymethyl-6-benzyloxy-5-((E)-2-methoxycarbonyl-vinylamino)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (176685-38-4) → CC-1065 (69866-21-3)

Conditions

Yield

Multi-step reaction with 7 steps 1: 23 percent / Pd(OAc)2 / N,N-dimethyl-acetamide / 70 °C 2: 48 percent / Me2SBH3 / tetrahydrofuran / 19 h / Heating 3: 82 percent / PPh3, CCl4 / CH2Cl2 / 7 h / Ambient temperature 4: 88 percent / 25percent HCO2NH4 / 10percentPd-C / tetrahydrofuran / 6 h / 0 °C 5: 3M HCl / ethyl acetate / 1 h / Ambient temperature 6: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature 7: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature View Scheme

N-(2-hydroxy-4-nitrophenyl)benzamide (38880-89-6) → CC-1065 (69866-21-3)

Conditions

Yield

Multi-step reaction with 18 steps 1: 94 percent / K2CO3 / n-Bu4NI / acetone / 16 h / Heating 2: 90 percent / Na2S2O4 / tetrahydrofuran; H2O / 30 h / Heating 3: pyridine / tetrahydrofuran / 18 h / 22 °C 4: 84 percent / lead tetraacetate / benzene / 8 h / 22 °C 5: CH2Cl2 / 10 h / 23 °C 6: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C 7: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C 8: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h 9: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating 10: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min 11: 83 percent / acetyl chloride / methanol / 2 h / 50 °C 12: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 13: tetrahydrofuran / 20 h / 23 °C 14: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 15: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 16: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 17: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 18: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme

N-[4-[(Z)-Benzenesulfonylimino]-2-benzyloxy-cyclohexa-2,5-dien-(Z)-ylidene]-benzamide (112764-62-2) → CC-1065 (69866-21-3)

Conditions

Yield

Multi-step reaction with 13 steps 1: 2.) 10percent aq. HCl / 1.) CH2Cl2, 0 - 23 deg C, 12 h 2.) THF, 23 deg C, 12 h 2: 97 percent / N-bromosuccinimide / H2SO4 / tetrahydrofuran / 1 h / -23 °C 3: 1.) NaH / 1.) DMF, 23 deg C, 15 min 2.) DMF, 23 deg C, 3 h 4: n-Bu3SnH / AIBN / benzene / 5 h / 80 °C 5: 1.) BH3*SMe2 2.) 2N aq. NaOH, 30percent H2O2 / 1.) THF, 0 - 23 deg C, 1 - 3 h 2.) 45 deg C, 30 min 6: 83 percent / 5percent HCl / methanol / 2 h / 50 °C 7: sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 3 h / 100 °C 8: tetrahydrofuran / 3 h / 23 °C 9: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C 10: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C 11: 3N HCl / ethyl acetate / 0.75 h / 23 °C 12: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C 13: Et3N / H2O; acetonitrile / 0.5 h / 23 °C View Scheme

5-amino-1-benzoyl-7-(benzyloxy)-3-methyl-N5-(phenylsulfonyl)indole (112764-63-3) → CC-1065 (69866-21-3)

Conditions	Yield
Multi-step reaction with 12 steps 1: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C 2: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h 3: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating 4: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min 5: 83 percent / acetyl chloride / methanol / 2 h / 50 °C 6: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 7: tetrahydrofuran / 20 h / 23 °C 8: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 9: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 10: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 11: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 12: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme
Multi-step reaction with 12 steps 1: 97 percent / N-bromosuccinimide / H2SO4 / tetrahydrofuran / 1 h / -23 °C 2: 1.) NaH / 1.) DMF, 23 deg C, 15 min 2.) DMF, 23 deg C, 3 h 3: n-Bu3SnH / AIBN / benzene / 5 h / 80 °C 4: 1.) BH3*SMe2 2.) 2N aq. NaOH, 30percent H2O2 / 1.) THF, 0 - 23 deg C, 1 - 3 h 2.) 45 deg C, 30 min 5: 83 percent / 5percent HCl / methanol / 2 h / 50 °C 6: sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 3 h / 100 °C 7: tetrahydrofuran / 3 h / 23 °C 8: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C 9: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C 10: 3N HCl / ethyl acetate / 0.75 h / 23 °C 11: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C 12: Et3N / H2O; acetonitrile / 0.5 h / 23 °C View Scheme

6-(6-Carbamoyl-5-hydroxy-4-methoxy-3,6,7,8-tetrahydro-pyrrolo[3,2-e]indole-2-carbonyl)-5-hydroxy-4-methoxy-3,6,7,8-tetrahydro-pyrrolo[3,2-e]indole-2-carboxylic acid (98296-23-2) → CC-1065 (69866-21-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 2: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme
Multi-step reaction with 2 steps 1: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C 2: Et3N / H2O; acetonitrile / 0.5 h / 23 °C View Scheme

N-(4-Amino-2-benzyloxy-phenyl)-benzamide (112764-73-5) → CC-1065 (69866-21-3)

Conditions

Yield

Multi-step reaction with 16 steps 1: pyridine / tetrahydrofuran / 18 h / 22 °C 2: 84 percent / lead tetraacetate / benzene / 8 h / 22 °C 3: CH2Cl2 / 10 h / 23 °C 4: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C 5: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C 6: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h 7: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating 8: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min 9: 83 percent / acetyl chloride / methanol / 2 h / 50 °C 10: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 11: tetrahydrofuran / 20 h / 23 °C 12: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 13: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 14: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 15: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 16: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme

N-(2-Benzyloxy-4-nitro-phenyl)-benzamide (112764-72-4) → CC-1065 (69866-21-3)

Conditions

Yield

Multi-step reaction with 17 steps 1: 90 percent / Na2S2O4 / tetrahydrofuran; H2O / 30 h / Heating 2: pyridine / tetrahydrofuran / 18 h / 22 °C 3: 84 percent / lead tetraacetate / benzene / 8 h / 22 °C 4: CH2Cl2 / 10 h / 23 °C 5: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C 6: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C 7: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h 8: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating 9: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min 10: 83 percent / acetyl chloride / methanol / 2 h / 50 °C 11: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 12: tetrahydrofuran / 20 h / 23 °C 13: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 14: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 15: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 16: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 17: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme

N-<4-(benzoylimino)-3-(benzyloxy)-2,5-cyclohexadien-1-ylidene>benzenesulfonamide → CC-1065 (69866-21-3)

Conditions

Yield

Multi-step reaction with 14 steps 1: CH2Cl2 / 10 h / 23 °C 2: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C 3: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C 4: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h 5: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating 6: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min 7: 83 percent / acetyl chloride / methanol / 2 h / 50 °C 8: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 9: tetrahydrofuran / 20 h / 23 °C 10: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 11: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 12: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 13: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 14: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme

N-(4-Benzenesulfonylamino-2-benzyloxy-phenyl)-benzamide (112764-74-6) → CC-1065 (69866-21-3)

Conditions

Yield

Multi-step reaction with 15 steps 1: 84 percent / lead tetraacetate / benzene / 8 h / 22 °C 2: CH2Cl2 / 10 h / 23 °C 3: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C 4: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C 5: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h 6: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating 7: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min 8: 83 percent / acetyl chloride / methanol / 2 h / 50 °C 9: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 10: tetrahydrofuran / 20 h / 23 °C 11: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 12: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 13: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 14: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 15: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme

N-(1-Benzoyl-7-benzyloxy-3-methyl-2-piperidin-1-yl-2,3-dihydro-1H-indol-5-yl)-benzenesulfonamide → CC-1065 (69866-21-3)

Conditions

Yield

Multi-step reaction with 13 steps 1: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C 2: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C 3: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h 4: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating 5: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min 6: 83 percent / acetyl chloride / methanol / 2 h / 50 °C 7: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 8: tetrahydrofuran / 20 h / 23 °C 9: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 10: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 11: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 12: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 13: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme

PDE I dimer methyl ester (107890-45-9) → CC-1065 (69866-21-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 84 percent / sodium dithionite, lithium hydroxide / tetrahydrofuran; methanol; H2O / 10 h / 45 °C 2: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 3: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme
Multi-step reaction with 3 steps 1: 84 percent / LiOH, Na2S2O4, water / tetrahydrofuran; methanol / 10 h / 45 °C 2: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C 3: Et3N / H2O; acetonitrile / 0.5 h / 23 °C View Scheme

5-(benzyloxy)-1,2,3,6-tetrahydro-8-methylbenzo<1,2-b:4,3-b'>dipyrrole-1-methanol (112243-83-1) → CC-1065 (69866-21-3)

Conditions	Yield
Multi-step reaction with 6 steps 1: tetrahydrofuran / 20 h / 23 °C 2: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 3: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 4: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 5: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 6: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme
Multi-step reaction with 6 steps 1: tetrahydrofuran / 3 h / 23 °C 2: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C 3: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C 4: 3N HCl / ethyl acetate / 0.75 h / 23 °C 5: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C 6: Et3N / H2O; acetonitrile / 0.5 h / 23 °C View Scheme

(1RS)-3-(Benzenesulfonyl)-5-(benzyloxy)-1-(hydroxymethyl)-8-methyl-1,2-dihydro-3H-pyrrolo<3,2-e>indole (112764-67-7) → CC-1065 (69866-21-3)

Conditions	Yield
Multi-step reaction with 7 steps 1: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 2: tetrahydrofuran / 20 h / 23 °C 3: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 4: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 5: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 6: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 7: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme
Multi-step reaction with 7 steps 1: sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 3 h / 100 °C 2: tetrahydrofuran / 3 h / 23 °C 3: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C 4: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C 5: 3N HCl / ethyl acetate / 0.75 h / 23 °C 6: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C 7: Et3N / H2O; acetonitrile / 0.5 h / 23 °C View Scheme

5-amino-1-benzoyl-7-(benzyloxy)-4-bromo-3-methyl-N5-(phenylsulfonyl)indole (112764-64-4) → CC-1065 (69866-21-3)

Conditions	Yield
Multi-step reaction with 11 steps 1: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h 2: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating 3: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min 4: 83 percent / acetyl chloride / methanol / 2 h / 50 °C 5: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 6: tetrahydrofuran / 20 h / 23 °C 7: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 8: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 9: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 10: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 11: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme
Multi-step reaction with 11 steps 1: 1.) NaH / 1.) DMF, 23 deg C, 15 min 2.) DMF, 23 deg C, 3 h 2: n-Bu3SnH / AIBN / benzene / 5 h / 80 °C 3: 1.) BH3*SMe2 2.) 2N aq. NaOH, 30percent H2O2 / 1.) THF, 0 - 23 deg C, 1 - 3 h 2.) 45 deg C, 30 min 4: 83 percent / 5percent HCl / methanol / 2 h / 50 °C 5: sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 3 h / 100 °C 6: tetrahydrofuran / 3 h / 23 °C 7: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C 8: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C 9: 3N HCl / ethyl acetate / 0.75 h / 23 °C 10: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C 11: Et3N / H2O; acetonitrile / 0.5 h / 23 °C View Scheme

6-benzoyl-5-(benzyloxy)-1,2-dihydro-8-methyl-1-methylidene-3-(phenylsulfonyl)-3H-pyrrolo<3,2-e>indole (112793-55-2) → CC-1065 (69866-21-3)

Conditions	Yield
Multi-step reaction with 9 steps 1: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min 2: 83 percent / acetyl chloride / methanol / 2 h / 50 °C 3: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 4: tetrahydrofuran / 20 h / 23 °C 5: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 6: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 7: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 8: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 9: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme
Multi-step reaction with 9 steps 1: 1.) BH3*SMe2 2.) 2N aq. NaOH, 30percent H2O2 / 1.) THF, 0 - 23 deg C, 1 - 3 h 2.) 45 deg C, 30 min 2: 83 percent / 5percent HCl / methanol / 2 h / 50 °C 3: sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 3 h / 100 °C 4: tetrahydrofuran / 3 h / 23 °C 5: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C 6: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C 7: 3N HCl / ethyl acetate / 0.75 h / 23 °C 8: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C 9: Et3N / H2O; acetonitrile / 0.5 h / 23 °C View Scheme

6-benzoyl-5-(benzyloxy)-1,2-dihydro-1-(hydroxymethyl)-8-methyl-3-(phenylsulfonyl)-3H-pyrrolo<3,2-e>indole (112764-66-6) → CC-1065 (69866-21-3)

Conditions	Yield
Multi-step reaction with 8 steps 1: 83 percent / acetyl chloride / methanol / 2 h / 50 °C 2: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 3: tetrahydrofuran / 20 h / 23 °C 4: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 5: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 6: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 7: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 8: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme
Multi-step reaction with 8 steps 1: 83 percent / 5percent HCl / methanol / 2 h / 50 °C 2: sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 3 h / 100 °C 3: tetrahydrofuran / 3 h / 23 °C 4: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C 5: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C 6: 3N HCl / ethyl acetate / 0.75 h / 23 °C 7: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C 8: Et3N / H2O; acetonitrile / 0.5 h / 23 °C View Scheme

1-benzoyl-7-(benzyloxy)-4-bromo-3-methyl-N5-(phenylsulfonyl)-5-(2-propyn-1-ylamino)indole (112764-65-5) → CC-1065 (69866-21-3)

Conditions	Yield
Multi-step reaction with 10 steps 1: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating 2: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min 3: 83 percent / acetyl chloride / methanol / 2 h / 50 °C 4: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 5: tetrahydrofuran / 20 h / 23 °C 6: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 7: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 8: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 9: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 10: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme
Multi-step reaction with 10 steps 1: n-Bu3SnH / AIBN / benzene / 5 h / 80 °C 2: 1.) BH3*SMe2 2.) 2N aq. NaOH, 30percent H2O2 / 1.) THF, 0 - 23 deg C, 1 - 3 h 2.) 45 deg C, 30 min 3: 83 percent / 5percent HCl / methanol / 2 h / 50 °C 4: sodium bis(2-methoxyethoxy)aluminium hydride / toluene / 3 h / 100 °C 5: tetrahydrofuran / 3 h / 23 °C 6: 87 percent / CCl4, Ph3P / CH2Cl2 / 12 h / 23 °C 7: 100 percent / aq. HCO2NH4 / 10percent Pd/C / tetrahydrofuran / 0.75 h / 23 °C 8: 3N HCl / ethyl acetate / 0.75 h / 23 °C 9: 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride, NaHCO3 / dimethylformamide / 24 h / 23 °C 10: Et3N / H2O; acetonitrile / 0.5 h / 23 °C View Scheme

2-Amino-5-nitrophenol (121-88-0) → CC-1065 (69866-21-3)

Conditions

Yield

Multi-step reaction with 19 steps 1: 92 percent / K2CO3 / 4-(dimethylamino)pyridine / tetrahydrofuran / 4 h / 23 °C 2: 94 percent / K2CO3 / n-Bu4NI / acetone / 16 h / Heating 3: 90 percent / Na2S2O4 / tetrahydrofuran; H2O / 30 h / Heating 4: pyridine / tetrahydrofuran / 18 h / 22 °C 5: 84 percent / lead tetraacetate / benzene / 8 h / 22 °C 6: CH2Cl2 / 10 h / 23 °C 7: 10percent aq. hydrochloric acid / tetrahydrofuran / 20 h / 23 °C 8: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C 9: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h 10: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating 11: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min 12: 83 percent / acetyl chloride / methanol / 2 h / 50 °C 13: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C 14: tetrahydrofuran / 20 h / 23 °C 15: triphenylphosphine, carbon tetrachloride / CH2Cl2 / 14 h / 23 °C 16: 100 percent / 25percent aq. ammonium formate / 10percent palladium/carbon / tetrahydrofuran / 0.5 h / 24 °C 17: 3 N hydrochloric acid / ethyl acetate / 0.75 h / 21 °C 18: 78 percent / sodium bicarbonate, EDCI / dimethylformamide / 22 h / 21 °C 19: 43 percent / Et3N / H2O; acetonitrile / 0.5 h / 22 °C View Scheme

((S)-5-Benzyloxy-8-methyl-1,2,3,6-tetrahydro-pyrrolo[3,2-e]indol-1-yl)-methanol (108833-14-3) → CC-1065 (69866-21-3)

Conditions

Yield

Multi-step reaction with 7 steps 1: triethylamine / tetrahydrofuran / 90 h 2: pyridine / 6 h / Ambient temperature 3: lithium chloride / dimethylformamide / 0.42 h / 80 °C 4: ammonium formate / 10percent Pd/C / tetrahydrofuran; methanol / 0.33 h / Ambient temperature 5: hydrogen chloride gas / ethyl acetate / 0.67 h 6: 54 percent / EDC / N,N-dimethyl-acetamide / 2 h / Ambient temperature 7: triethylamine / acetonitrile; H2O / 1 h / Ambient temperature View Scheme

((S)-5-Benzyloxy-3-methanesulfonyl-8-methyl-1,2,3,6-tetrahydro-pyrrolo[3,2-e]indol-1-yl)-methanol (101222-79-1) → CC-1065 (69866-21-3)

Conditions

Yield

Multi-step reaction with 8 steps 1: 3.4 M REDAL / tetrahydrofuran; toluene / 0.5 h / 85 °C 2: triethylamine / tetrahydrofuran / 90 h 3: pyridine / 6 h / Ambient temperature 4: lithium chloride / dimethylformamide / 0.42 h / 80 °C 5: ammonium formate / 10percent Pd/C / tetrahydrofuran; methanol / 0.33 h / Ambient temperature 6: hydrogen chloride gas / ethyl acetate / 0.67 h 7: 54 percent / EDC / N,N-dimethyl-acetamide / 2 h / Ambient temperature 8: triethylamine / acetonitrile; H2O / 1 h / Ambient temperature View Scheme

(S)-5-Benzyloxy-1-methanesulfonyloxymethyl-8-methyl-1,6-dihydro-2H-pyrrolo[3,2-e]indole-3-carboxylic acid tert-butyl ester (110314-49-3) → CC-1065 (69866-21-3)

Conditions	Yield
Multi-step reaction with 5 steps 1: lithium chloride / dimethylformamide / 0.42 h / 80 °C 2: ammonium formate / 10percent Pd/C / tetrahydrofuran; methanol / 0.33 h / Ambient temperature 3: hydrogen chloride gas / ethyl acetate / 0.67 h 4: 54 percent / EDC / N,N-dimethyl-acetamide / 2 h / Ambient temperature 5: triethylamine / acetonitrile; H2O / 1 h / Ambient temperature View Scheme

C18H15ClN2O5S → CC-1065 (69866-21-3)

Conditions

Yield

Multi-step reaction with 15 steps 1.1: dichloromethane; dimethyl sulfoxide / 29 h / 0 °C 2.1: diisobutylaluminium hydride / toluene / 2.5 h / -78 °C 2.2: 2.5 h / -78 °C 3.1: dmap / acetonitrile / 1 h / 20 °C 4.1: sodium chlorite; 2-methyl-but-2-ene; sodium dihydrogenphosphate / tetrahydrofuran; water; tert-butyl alcohol / 12 h / 20 °C 5.1: dmap; dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 8 h / 20 °C 6.1: sodium cyanoborohydride; acetic acid / 1,2-dichloro-benzene / 8.5 h / 185 °C 7.1: sodium hydrogencarbonate / tetrahydrofuran / 0.33 h / 20 °C 8.1: boron trichloride / dichloromethane / 0.67 h / 0 °C 9.1: palladium 10% on activated carbon; hydrogen / ethanol / 17 h / 20 °C / 760.05 Torr 10.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 10 h / 20 °C 11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C 12.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; tetrahydrofuran / 4 h / 20 °C 12.2: 1 h / 20 °C 13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3.25 h / 20 °C 13.2: 4.17 h / 0 - 20 °C 14.1: hydrogen; 10 wt% Pd(OH)2 on carbon / tetrahydrofuran / 0.33 h / 20 °C 15.1: triethylamine / tetrahydrofuran / 1 h / 20 °C View Scheme

C13H11N3O2 → CC-1065 (69866-21-3)

Conditions

Yield

Multi-step reaction with 14 steps 1.1: diisobutylaluminium hydride / toluene / 2.5 h / -78 °C 1.2: 2.5 h / -78 °C 2.1: dmap / acetonitrile / 1 h / 20 °C 3.1: sodium chlorite; 2-methyl-but-2-ene; sodium dihydrogenphosphate / tetrahydrofuran; water; tert-butyl alcohol / 12 h / 20 °C 4.1: dmap; dicyclohexyl-carbodiimide / N,N-dimethyl-formamide / 8 h / 20 °C 5.1: sodium cyanoborohydride; acetic acid / 1,2-dichloro-benzene / 8.5 h / 185 °C 6.1: sodium hydrogencarbonate / tetrahydrofuran / 0.33 h / 20 °C 7.1: boron trichloride / dichloromethane / 0.67 h / 0 °C 8.1: palladium 10% on activated carbon; hydrogen / ethanol / 17 h / 20 °C / 760.05 Torr 9.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 10 h / 20 °C 10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C 11.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; tetrahydrofuran / 4 h / 20 °C 11.2: 1 h / 20 °C 12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3.25 h / 20 °C 12.2: 4.17 h / 0 - 20 °C 13.1: hydrogen; 10 wt% Pd(OH)2 on carbon / tetrahydrofuran / 0.33 h / 20 °C 14.1: triethylamine / tetrahydrofuran / 1 h / 20 °C View Scheme

CC-1065 (69866-21-3) → C37H35N7O9

Conditions	Yield
With water In aq. phosphate buffer; dimethyl sulfoxide at 25℃; pH=7.0; Reagent/catalyst; Enzymatic reaction;

Upstream product

• 112764-73-5 N-(4-Amino-2-benzyloxy-phenyl)-benzamide 
• 112764-72-4 N-(2-Benzyloxy-4-nitro-phenyl)-benzamide 
• 898530-72-8 (+)-[(2S)-3-azido-1-(4-benzyloxy-2,6-dibromophenyl)propan-2-yloxy](tert-butyl)dimethylsilane 

Relevant academic research and scientific papers

Total Synthesis of (+)-CC-1065 Utilizing Ring Expansion Reaction of Benzocyclobutenone Oxime Sulfonate

An indole synthesis via ring expansion of benzocyclobutenone oxime sulfonate was developed. Utility of the indole synthesis was demonstrated by the total synthesis of (+)-CC-1065. The middle and right segments were constructed by a sequential ring expansion of the symmetrical benzo-bis-cyclobutenone. The left segment was also constructed via ring expansion of the methyl-substituted benzocyclobutenone oxime sulfonates. After condensation of these three segments, the dienone cyclopropane structure was formed to complete the total synthesis.

Novel syntheses of optically active CC-1065, U-73,975(adozelesin), U-80,244(carzelesin), U-77,779(bizelesin), KW-2189, and DU-86

The title syntheses were achieved by the method featuring oxidative cyclization of the enamino esters [(S)-13 and (S)-24] derived from the 5-aminoindoline [(5)-12], acylation with various structural types of indole-2-carboxylic acids, and formation of cyclopropapyrroloindole moieties.