CAS No.130288-24-3,Duocarmycin SA Suppliers

Qingdao Beluga Import and Export Co., LTD

Duocarmycin SA CAS:130288-24-3 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in high quality organic intermed

Duocarmycin SA CAS:130288-24-3

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Shandong Hanjiang Chemical Co., Ltd.

Hello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai

Cyclopropa[c]pyrrolo[3,2-e]indole-6-carboxylicacid,1,2,4,5,8,8a-hexahydro-4-oxo-2-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-,methyl ester, (7bR,8aS)-

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Henan Wentao Chemical Product Co., Ltd.

Henan Wentao Chemical Product Co.,Ltd is Located in Zhengzhou High-tech Development Zone with import and export license, We passed ISO 9001:2008 as well, Henan Wentao has developed more than 1000 compounds, which are widely used in the fields of prod

Cyclopropa[c]pyrrolo[3,2-e]indole-6-carboxylicacid,1,2,4,5,8,8a-hexahydro-4-oxo-2-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-,methyl ester, (7bR,8aS)-

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Zibo Hangyu Biotechnology Development Co., Ltd

Zibo Hangyu Biotechnology Development Co., Ltd is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemi

Cyclopropa[c]pyrrolo[3,2-e]indole-6-carboxylicacid,1,2,4,5,8,8a-hexahydro-4-oxo-2-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-,methyl ester, (7bR,8aS)-

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Xi`an Eastling Biotech Co., Ltd.

high purity lowest priceAppearance:solid or liquid Storage:in sealed air resistant place Package:Foil bag; Drum; Plastic bottle Application:Pharma;Industry;Agricultural Transportation:by sea or air Port:Beijing or Guangzhou

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Henan Tianfu Chemical Co., Ltd.

1.Our services：A.Supply sampleB.The packing also can be according the customers` requirmentC.Any inquiries will be replied within 24 hoursD.we provide Commerical Invoice, Packing List, Bill of loading, COA , Health certificate and Origin certificate.

Cyclopropa[c]pyrrolo[3,2-e]indole-6-carboxylicacid,1,2,4,5,8,8a-hexahydro-4-oxo-2-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-,methyl ester, (7bR,8aS)-

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Antimex Chemical Limied

Ansciep Chemical is a professional enterprise manufacturing and distributing fine chemicals and speciality chemicals. We have been dedicated to heterocycle compounds and phenyl rings for tens of years. This is our mature product for export. Our quali

Cyclopropa[c]pyrrolo[3,2-e]indole-6-carboxylicacid,1,2,4,5,8,8a-hexahydro-4-oxo-2-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-,methyl ester, (7bR,8aS)-

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Guangdong Juda Chemical Industrial Co.,Limited

Appearance:solid or liquid Storage:sealed in cool and dry place Package:As customer's requested Application:Pharma Intermediate Transportation:by courier/air/sea Port:Any port in China

Duocarmycin SA CAS No.130288-24-3

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Wuhan Circle Star Chem-medical Technology co.,Ltd.

good quality, competitive price, thoughtful after sale serviceAppearance:white powder Storage:Keep it in dry,shady and cool place Package:25kg,50kg,180kg,200kg,250kg,1000kg，customization Application:Pharma;Industry;Agricultural;chemical reaserch Tran

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Hangzhou Fandachem Co.,Ltd

(7BR)-1,2,4,5,8,8A-HEXAHYDRO-4-OXO-2-[(5,6,7-TRIMETHOXY-1H-INDOL-2-YL)CARBONYL]-CYCLOPROPA[C]PYRROLO[3,2-E]INDOLE-6-CARBOXYLIC ACID METHYL ESTERCASAppearance:white crystalline powder Storage:Store in dry, dark and ventilated place Package:25KG drum A

(7BR)-1,2,4,5,8,8A-HEXAHYDRO-4-OXO-2-[(5,6,7-TRIMETHOXY-1H-INDOL-2-YL)CARBONYL]-CYCLOPROPA[C]PYRROLO[3,2-E]INDOLE-6-CARBOXYLIC ACID METHYL ESTERCAS

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Henan Kanbei Chemical Co.,LTD

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Shanghai Chinqesen Biotechnology Co., Ltd.

Good Quality Package:1kg/bag Application:Medical or chemical Transportation:Air/Train/Sea Port:Shenzhen

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ZHEJIANG JIUZHOU CHEM CO.,LTD

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Nanjing Raymon Biotech Co., Ltd.

Cyclopropa[c]pyrrolo[3,2-e]indole-6-carboxylicacid,1,2,4,5,8,8a-hexahydro-4-oxo-2-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-,methyl ester, (7bR,8aS)- Storage:keep in dry and cool condition Package:25kg or according to cutomer's demand Application:Ch

Cyclopropa[c]pyrrolo[3,2-e]indole-6-carboxylicacid,1,2,4,5,8,8a-hexahydro-4-oxo-2-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-,methyl ester, (7bR,8aS)-

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Hebei Ruishun Trade Co.,Ltd

Supply top quality products with a reasonable price Application:api

130288-24-3

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Chemical Co.Ltd

Cyclopropa[c]pyrrolo[3,2-e]indole-6-carboxylicacid,1,2,4,5,8,8a-hexahydro-4-oxo-2-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-,methyl ester, (7bR,8aS)-Appearance:Off white to slight yellow solid Storage:Stored in shaded, cool and dry places Package:1L

Cyclopropa[c]pyrrolo[3,2-e]indole-6-carboxylicacid,1,2,4,5,8,8a-hexahydro-4-oxo-2-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-,methyl ester, (7bR,8aS)-

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Synthetic route

: methyl (S)-4-hydroxy-8-(hydroxymethyl)-6-(5,6,7-trimethoxy-1Hindole-2-carbonyl)-3,6,7,8-tetrahydropyrrolo[3,2-e]indole-2-carboxylate

: 130288-24-3
(+)-duocarmycin SA

Conditions

Conditions	Yield
With tributylphosphine; azodicarbonyl dimorpholide In tetrahydrofuran for 2h; Inert atmosphere; enantioselective reaction;	94%
With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine In tetrahydrofuran for 0.333333h; Inert atmosphere;

: (8S)-4-hydroxy-8-methanesulfonyloxymethyl-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-3,6,7,8-tetrahydro-3,6-diaza-as-indacene-2-carboxylic acid methyl ester

: 130288-24-3
(+)-duocarmycin SA

Conditions

Conditions	Yield
With caesium carbonate In acetonitrile at 23℃; for 1h;	92%

: 144667-38-9
duocarmycin

: 130288-24-3
(+)-duocarmycin SA

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 3h; Ambient temperature;	91%
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; for 0.5h;	87%
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; for 30h;
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 25℃; for 1h;

: 919535-11-8
methyl (S)-4-[(5,6,7-trimethoxyindol-2yl)carbonyl]-2,6-dihydroxy-1,2,3,4-tetrahydropyrrolo[3,2-f]quinoline-8-carboxylate

: 130288-24-3
(+)-duocarmycin SA

Conditions

Conditions	Yield
With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine In tetrahydrofuran at 25℃; for 0.5h; Mitsunobu reaction;	62%

: (R)-8-Chloromethyl-4-hydroxy-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-3,6,7,8-tetrahydro-pyrrolo[3,2-e]indole-2-carboxylic acid methyl ester

: 130288-24-3
(+)-duocarmycin SA

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; for 30h;

: C13H12N2O3

: 157425-68-8
1-(5,6,7-trimethoxyindole-2-carbonyl)imidazole

: 130288-24-3
(+)-duocarmycin SA

Conditions

Conditions	Yield
With sodium hydride 1.) DMF, THF, 2.) DMF, THF, 0 deg C; Yield given. Multistep reaction;

: 150992-82-8
(+)-(7bR,8aS)-methyl 4-oxo-1,2,4,5,8,8a-hexahydrocyclopropapyrrolo<3,2-e>indole-6-carboxylate

: 157425-68-8
1-(5,6,7-trimethoxyindole-2-carbonyl)imidazole

: 130288-24-3
(+)-duocarmycin SA

Conditions

Conditions	Yield
With sodium hydride 1.) DMF-THF, 2.) 0 deg C; Yield given. Multistep reaction;
With sodium hydride 1.) THF, DMF, 0 deg C, 20 min, 2.) THF, DMF, 0 deg C, 4 h; Yield given. Multistep reaction;

: 151062-83-8
methyl (7bS)-(-)-1,2,4,5,8,8a-hexahydro-4-oxocyclopropapyrrolo<3,2-e>indole-6-carboxylate

: 157425-68-8
1-(5,6,7-trimethoxyindole-2-carbonyl)imidazole

: 130288-24-3
(+)-duocarmycin SA

Conditions

Conditions	Yield
With sodium hydride 1.) THF, DMF, 0 deg C, 20 min, 2.) THF, DMF, 0 deg C, 4 h; Yield given. Multistep reaction;

: 881422-32-8
3-(benzyloxy)-5-nitrobenzaldehyde

A: 130288-24-3
(+)-duocarmycin SA

B calf thymus DNA: calf thymus DNA

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1.1: 78 percent / NaOMe / methanol; tetrahydrofuran / 17 h / -25 °C 2.1: 68 percent / xylene / 7 h / 140 °C 3.1: 98 percent / DMAP / tetrahydrofuran / 1 h / 25 °C 4.1: 98 percent / Zn; NH4Cl / acetone; H2O / 0.5 h / 25 °C 5.1: 227 mg / tetrahydrofuran / 10 h / 25 °C 6.1: 91 percent / N-iodosuccinimide; AcOH / toluene / 8 h / 25 °C 7.1: 96 percent / NaH / dimethylformamide / 2 h / 0 °C 8.1: i-PrMgBr / tetrahydrofuran / 1 h / -40 °C 8.2: 69 percent / CuI; Bu3P / tetrahydrofuran / 1.5 h / -78 - -40 °C 9.1: 82 percent / H2 / Pd/C / methanol; tetrahydrofuran / 0.5 h / 25 °C 10.1: HCl / ethyl acetate / 3 h / 25 °C 11.1: 3.7 mg / EDCI / dimethylformamide / 2 h / 0 °C 12.1: 62 percent / Bu3P; ADDP / tetrahydrofuran / 0.5 h / 25 °C View Scheme

Yield

Multi-step reaction with 12 steps
1.1: 78 percent / NaOMe / methanol; tetrahydrofuran / 17 h / -25 °C
2.1: 68 percent / xylene / 7 h / 140 °C
3.1: 98 percent / DMAP / tetrahydrofuran / 1 h / 25 °C
4.1: 98 percent / Zn; NH4Cl / acetone; H2O / 0.5 h / 25 °C
5.1: 227 mg / tetrahydrofuran / 10 h / 25 °C
6.1: 91 percent / N-iodosuccinimide; AcOH / toluene / 8 h / 25 °C
7.1: 96 percent / NaH / dimethylformamide / 2 h / 0 °C
8.1: i-PrMgBr / tetrahydrofuran / 1 h / -40 °C
8.2: 69 percent / CuI; Bu3P / tetrahydrofuran / 1.5 h / -78 - -40 °C
9.1: 82 percent / H2 / Pd/C / methanol; tetrahydrofuran / 0.5 h / 25 °C
10.1: HCl / ethyl acetate / 3 h / 25 °C
11.1: 3.7 mg / EDCI / dimethylformamide / 2 h / 0 °C
12.1: 62 percent / Bu3P; ADDP / tetrahydrofuran / 0.5 h / 25 °C
View Scheme

: methyl 2-azido-3-(3-benzyloxy-5-nitrophenyl)acrylate

A: 130288-24-3
(+)-duocarmycin SA

B calf thymus DNA: calf thymus DNA

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1.1: 68 percent / xylene / 7 h / 140 °C 2.1: 98 percent / DMAP / tetrahydrofuran / 1 h / 25 °C 3.1: 98 percent / Zn; NH4Cl / acetone; H2O / 0.5 h / 25 °C 4.1: 227 mg / tetrahydrofuran / 10 h / 25 °C 5.1: 91 percent / N-iodosuccinimide; AcOH / toluene / 8 h / 25 °C 6.1: 96 percent / NaH / dimethylformamide / 2 h / 0 °C 7.1: i-PrMgBr / tetrahydrofuran / 1 h / -40 °C 7.2: 69 percent / CuI; Bu3P / tetrahydrofuran / 1.5 h / -78 - -40 °C 8.1: 82 percent / H2 / Pd/C / methanol; tetrahydrofuran / 0.5 h / 25 °C 9.1: HCl / ethyl acetate / 3 h / 25 °C 10.1: 3.7 mg / EDCI / dimethylformamide / 2 h / 0 °C 11.1: 62 percent / Bu3P; ADDP / tetrahydrofuran / 0.5 h / 25 °C View Scheme

Yield

Multi-step reaction with 11 steps
1.1: 68 percent / xylene / 7 h / 140 °C
2.1: 98 percent / DMAP / tetrahydrofuran / 1 h / 25 °C
3.1: 98 percent / Zn; NH4Cl / acetone; H2O / 0.5 h / 25 °C
4.1: 227 mg / tetrahydrofuran / 10 h / 25 °C
5.1: 91 percent / N-iodosuccinimide; AcOH / toluene / 8 h / 25 °C
6.1: 96 percent / NaH / dimethylformamide / 2 h / 0 °C
7.1: i-PrMgBr / tetrahydrofuran / 1 h / -40 °C
7.2: 69 percent / CuI; Bu3P / tetrahydrofuran / 1.5 h / -78 - -40 °C
8.1: 82 percent / H2 / Pd/C / methanol; tetrahydrofuran / 0.5 h / 25 °C
9.1: HCl / ethyl acetate / 3 h / 25 °C
10.1: 3.7 mg / EDCI / dimethylformamide / 2 h / 0 °C
11.1: 62 percent / Bu3P; ADDP / tetrahydrofuran / 0.5 h / 25 °C
View Scheme

: 4,8-dihydroxy-6,7,8,9-tetrahydro-3H-pyrrolo[3,2-f]quinoline-2-carboxylic acid methyl ester

A: 130288-24-3
(+)-duocarmycin SA

B calf thymus DNA: calf thymus DNA

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 3.7 mg / EDCI / dimethylformamide / 2 h / 0 °C 2: 62 percent / Bu3P; ADDP / tetrahydrofuran / 0.5 h / 25 °C View Scheme

: 919535-09-4
methyl (S)-4,7-di-tert-butoxycarbonyl-2,6-dihydroxy-1,2,3,4-tetrahydropyrrolo[3,2-f]quinoline-8-carboxylate

A: 130288-24-3
(+)-duocarmycin SA

B calf thymus DNA: calf thymus DNA

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: HCl / ethyl acetate / 3 h / 25 °C 2: 3.7 mg / EDCI / dimethylformamide / 2 h / 0 °C 3: 62 percent / Bu3P; ADDP / tetrahydrofuran / 0.5 h / 25 °C View Scheme

: 919535-06-1
1-(1,1-dimethylethyl)-2-methyl 5-[[(1,1-dimethylethoxy)-carbonyl]amino]-4-iodo-7-(phenylmethoxy)indole-1,2-dicarboxylate

A: 130288-24-3
(+)-duocarmycin SA

B calf thymus DNA: calf thymus DNA

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: 96 percent / NaH / dimethylformamide / 2 h / 0 °C 2.1: i-PrMgBr / tetrahydrofuran / 1 h / -40 °C 2.2: 69 percent / CuI; Bu3P / tetrahydrofuran / 1.5 h / -78 - -40 °C 3.1: 82 percent / H2 / Pd/C / methanol; tetrahydrofuran / 0.5 h / 25 °C 4.1: HCl / ethyl acetate / 3 h / 25 °C 5.1: 3.7 mg / EDCI / dimethylformamide / 2 h / 0 °C 6.1: 62 percent / Bu3P; ADDP / tetrahydrofuran / 0.5 h / 25 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: 96 percent / NaH / dimethylformamide / 2 h / 0 °C
2.1: i-PrMgBr / tetrahydrofuran / 1 h / -40 °C
2.2: 69 percent / CuI; Bu3P / tetrahydrofuran / 1.5 h / -78 - -40 °C
3.1: 82 percent / H2 / Pd/C / methanol; tetrahydrofuran / 0.5 h / 25 °C
4.1: HCl / ethyl acetate / 3 h / 25 °C
5.1: 3.7 mg / EDCI / dimethylformamide / 2 h / 0 °C
6.1: 62 percent / Bu3P; ADDP / tetrahydrofuran / 0.5 h / 25 °C
View Scheme

: 919535-08-3
methyl (S)-4,7-di-tert-butoxycarbonyl-6-benzyloxy-2-hydroxy-1,2,3,4-tetrahydropyrrolo[3,2-f]quinoline-8-carboxylate

A: 130288-24-3
(+)-duocarmycin SA

B calf thymus DNA: calf thymus DNA

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 82 percent / H2 / Pd/C / methanol; tetrahydrofuran / 0.5 h / 25 °C 2: HCl / ethyl acetate / 3 h / 25 °C 3: 3.7 mg / EDCI / dimethylformamide / 2 h / 0 °C 4: 62 percent / Bu3P; ADDP / tetrahydrofuran / 0.5 h / 25 °C View Scheme

: 919535-07-2
methyl (R)-7-benzyloxy-1-(tert-butoxycarbonyl)-5-(tert-butoxycarbonyl-(oxiran-2-ylmethyl)amino)-4-iodoindole-2-carboxylate

A: 130288-24-3
(+)-duocarmycin SA

B calf thymus DNA: calf thymus DNA

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: i-PrMgBr / tetrahydrofuran / 1 h / -40 °C 1.2: 69 percent / CuI; Bu3P / tetrahydrofuran / 1.5 h / -78 - -40 °C 2.1: 82 percent / H2 / Pd/C / methanol; tetrahydrofuran / 0.5 h / 25 °C 3.1: HCl / ethyl acetate / 3 h / 25 °C 4.1: 3.7 mg / EDCI / dimethylformamide / 2 h / 0 °C 5.1: 62 percent / Bu3P; ADDP / tetrahydrofuran / 0.5 h / 25 °C View Scheme

: 14193-18-1
3,5-dinitrobenzaldehyde

A: 130288-24-3
(+)-duocarmycin SA

B calf thymus DNA: calf thymus DNA

Conditions

Conditions	Yield
Multi-step reaction with 13 steps 1.1: syn-benzaldehyde oxime; K2CO3 / dimethylformamide / 1.25 h / 90 °C 1.2: 86 percent / dimethylformamide / 2 h / 25 °C 2.1: 78 percent / NaOMe / methanol; tetrahydrofuran / 17 h / -25 °C 3.1: 68 percent / xylene / 7 h / 140 °C 4.1: 98 percent / DMAP / tetrahydrofuran / 1 h / 25 °C 5.1: 98 percent / Zn; NH4Cl / acetone; H2O / 0.5 h / 25 °C 6.1: 227 mg / tetrahydrofuran / 10 h / 25 °C 7.1: 91 percent / N-iodosuccinimide; AcOH / toluene / 8 h / 25 °C 8.1: 96 percent / NaH / dimethylformamide / 2 h / 0 °C 9.1: i-PrMgBr / tetrahydrofuran / 1 h / -40 °C 9.2: 69 percent / CuI; Bu3P / tetrahydrofuran / 1.5 h / -78 - -40 °C 10.1: 82 percent / H2 / Pd/C / methanol; tetrahydrofuran / 0.5 h / 25 °C 11.1: HCl / ethyl acetate / 3 h / 25 °C 12.1: 3.7 mg / EDCI / dimethylformamide / 2 h / 0 °C 13.1: 62 percent / Bu3P; ADDP / tetrahydrofuran / 0.5 h / 25 °C View Scheme

Yield

Multi-step reaction with 13 steps
1.1: syn-benzaldehyde oxime; K2CO3 / dimethylformamide / 1.25 h / 90 °C
1.2: 86 percent / dimethylformamide / 2 h / 25 °C
2.1: 78 percent / NaOMe / methanol; tetrahydrofuran / 17 h / -25 °C
3.1: 68 percent / xylene / 7 h / 140 °C
4.1: 98 percent / DMAP / tetrahydrofuran / 1 h / 25 °C
5.1: 98 percent / Zn; NH4Cl / acetone; H2O / 0.5 h / 25 °C
6.1: 227 mg / tetrahydrofuran / 10 h / 25 °C
7.1: 91 percent / N-iodosuccinimide; AcOH / toluene / 8 h / 25 °C
8.1: 96 percent / NaH / dimethylformamide / 2 h / 0 °C
9.1: i-PrMgBr / tetrahydrofuran / 1 h / -40 °C
9.2: 69 percent / CuI; Bu3P / tetrahydrofuran / 1.5 h / -78 - -40 °C
10.1: 82 percent / H2 / Pd/C / methanol; tetrahydrofuran / 0.5 h / 25 °C
11.1: HCl / ethyl acetate / 3 h / 25 °C
12.1: 3.7 mg / EDCI / dimethylformamide / 2 h / 0 °C
13.1: 62 percent / Bu3P; ADDP / tetrahydrofuran / 0.5 h / 25 °C
View Scheme

: 539856-42-3
methyl 7-(benzyloxy)-5-nitro-1H-indole-2-carboxylate

A: 130288-24-3
(+)-duocarmycin SA

B calf thymus DNA: calf thymus DNA

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1.1: 98 percent / DMAP / tetrahydrofuran / 1 h / 25 °C 2.1: 98 percent / Zn; NH4Cl / acetone; H2O / 0.5 h / 25 °C 3.1: 227 mg / tetrahydrofuran / 10 h / 25 °C 4.1: 91 percent / N-iodosuccinimide; AcOH / toluene / 8 h / 25 °C 5.1: 96 percent / NaH / dimethylformamide / 2 h / 0 °C 6.1: i-PrMgBr / tetrahydrofuran / 1 h / -40 °C 6.2: 69 percent / CuI; Bu3P / tetrahydrofuran / 1.5 h / -78 - -40 °C 7.1: 82 percent / H2 / Pd/C / methanol; tetrahydrofuran / 0.5 h / 25 °C 8.1: HCl / ethyl acetate / 3 h / 25 °C 9.1: 3.7 mg / EDCI / dimethylformamide / 2 h / 0 °C 10.1: 62 percent / Bu3P; ADDP / tetrahydrofuran / 0.5 h / 25 °C View Scheme

Yield

Multi-step reaction with 10 steps
1.1: 98 percent / DMAP / tetrahydrofuran / 1 h / 25 °C
2.1: 98 percent / Zn; NH4Cl / acetone; H2O / 0.5 h / 25 °C
3.1: 227 mg / tetrahydrofuran / 10 h / 25 °C
4.1: 91 percent / N-iodosuccinimide; AcOH / toluene / 8 h / 25 °C
5.1: 96 percent / NaH / dimethylformamide / 2 h / 0 °C
6.1: i-PrMgBr / tetrahydrofuran / 1 h / -40 °C
6.2: 69 percent / CuI; Bu3P / tetrahydrofuran / 1.5 h / -78 - -40 °C
7.1: 82 percent / H2 / Pd/C / methanol; tetrahydrofuran / 0.5 h / 25 °C
8.1: HCl / ethyl acetate / 3 h / 25 °C
9.1: 3.7 mg / EDCI / dimethylformamide / 2 h / 0 °C
10.1: 62 percent / Bu3P; ADDP / tetrahydrofuran / 0.5 h / 25 °C
View Scheme

: 539856-49-0
1-(1,1-dimethylethyl)-2-methyl-5-nitro-6-(phenylmethoxy)-indole-1,2-dicarboxylate

A: 130288-24-3
(+)-duocarmycin SA

B calf thymus DNA: calf thymus DNA

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1.1: 98 percent / Zn; NH4Cl / acetone; H2O / 0.5 h / 25 °C 2.1: 227 mg / tetrahydrofuran / 10 h / 25 °C 3.1: 91 percent / N-iodosuccinimide; AcOH / toluene / 8 h / 25 °C 4.1: 96 percent / NaH / dimethylformamide / 2 h / 0 °C 5.1: i-PrMgBr / tetrahydrofuran / 1 h / -40 °C 5.2: 69 percent / CuI; Bu3P / tetrahydrofuran / 1.5 h / -78 - -40 °C 6.1: 82 percent / H2 / Pd/C / methanol; tetrahydrofuran / 0.5 h / 25 °C 7.1: HCl / ethyl acetate / 3 h / 25 °C 8.1: 3.7 mg / EDCI / dimethylformamide / 2 h / 0 °C 9.1: 62 percent / Bu3P; ADDP / tetrahydrofuran / 0.5 h / 25 °C View Scheme

Yield

Multi-step reaction with 9 steps
1.1: 98 percent / Zn; NH4Cl / acetone; H2O / 0.5 h / 25 °C
2.1: 227 mg / tetrahydrofuran / 10 h / 25 °C
3.1: 91 percent / N-iodosuccinimide; AcOH / toluene / 8 h / 25 °C
4.1: 96 percent / NaH / dimethylformamide / 2 h / 0 °C
5.1: i-PrMgBr / tetrahydrofuran / 1 h / -40 °C
5.2: 69 percent / CuI; Bu3P / tetrahydrofuran / 1.5 h / -78 - -40 °C
6.1: 82 percent / H2 / Pd/C / methanol; tetrahydrofuran / 0.5 h / 25 °C
7.1: HCl / ethyl acetate / 3 h / 25 °C
8.1: 3.7 mg / EDCI / dimethylformamide / 2 h / 0 °C
9.1: 62 percent / Bu3P; ADDP / tetrahydrofuran / 0.5 h / 25 °C
View Scheme

: 539856-43-4
methyl 5-amino-7-(benzyloxy)-1-(tert-butoxycarbonyl)indole-2-carboxylate

A: 130288-24-3
(+)-duocarmycin SA

B calf thymus DNA: calf thymus DNA

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: 227 mg / tetrahydrofuran / 10 h / 25 °C 2.1: 91 percent / N-iodosuccinimide; AcOH / toluene / 8 h / 25 °C 3.1: 96 percent / NaH / dimethylformamide / 2 h / 0 °C 4.1: i-PrMgBr / tetrahydrofuran / 1 h / -40 °C 4.2: 69 percent / CuI; Bu3P / tetrahydrofuran / 1.5 h / -78 - -40 °C 5.1: 82 percent / H2 / Pd/C / methanol; tetrahydrofuran / 0.5 h / 25 °C 6.1: HCl / ethyl acetate / 3 h / 25 °C 7.1: 3.7 mg / EDCI / dimethylformamide / 2 h / 0 °C 8.1: 62 percent / Bu3P; ADDP / tetrahydrofuran / 0.5 h / 25 °C View Scheme

Yield

Multi-step reaction with 8 steps
1.1: 227 mg / tetrahydrofuran / 10 h / 25 °C
2.1: 91 percent / N-iodosuccinimide; AcOH / toluene / 8 h / 25 °C
3.1: 96 percent / NaH / dimethylformamide / 2 h / 0 °C
4.1: i-PrMgBr / tetrahydrofuran / 1 h / -40 °C
4.2: 69 percent / CuI; Bu3P / tetrahydrofuran / 1.5 h / -78 - -40 °C
5.1: 82 percent / H2 / Pd/C / methanol; tetrahydrofuran / 0.5 h / 25 °C
6.1: HCl / ethyl acetate / 3 h / 25 °C
7.1: 3.7 mg / EDCI / dimethylformamide / 2 h / 0 °C
8.1: 62 percent / Bu3P; ADDP / tetrahydrofuran / 0.5 h / 25 °C
View Scheme

: 539856-50-3
methyl 7-(benzyloxy)-1-(tert-butoxycarbonyl)-5-[(tert-butoxycarbonyl)amino]indole-2-carboxylate

A: 130288-24-3
(+)-duocarmycin SA

B calf thymus DNA: calf thymus DNA

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: 91 percent / N-iodosuccinimide; AcOH / toluene / 8 h / 25 °C 2.1: 96 percent / NaH / dimethylformamide / 2 h / 0 °C 3.1: i-PrMgBr / tetrahydrofuran / 1 h / -40 °C 3.2: 69 percent / CuI; Bu3P / tetrahydrofuran / 1.5 h / -78 - -40 °C 4.1: 82 percent / H2 / Pd/C / methanol; tetrahydrofuran / 0.5 h / 25 °C 5.1: HCl / ethyl acetate / 3 h / 25 °C 6.1: 3.7 mg / EDCI / dimethylformamide / 2 h / 0 °C 7.1: 62 percent / Bu3P; ADDP / tetrahydrofuran / 0.5 h / 25 °C View Scheme

Yield

Multi-step reaction with 7 steps
1.1: 91 percent / N-iodosuccinimide; AcOH / toluene / 8 h / 25 °C
2.1: 96 percent / NaH / dimethylformamide / 2 h / 0 °C
3.1: i-PrMgBr / tetrahydrofuran / 1 h / -40 °C
3.2: 69 percent / CuI; Bu3P / tetrahydrofuran / 1.5 h / -78 - -40 °C
4.1: 82 percent / H2 / Pd/C / methanol; tetrahydrofuran / 0.5 h / 25 °C
5.1: HCl / ethyl acetate / 3 h / 25 °C
6.1: 3.7 mg / EDCI / dimethylformamide / 2 h / 0 °C
7.1: 62 percent / Bu3P; ADDP / tetrahydrofuran / 0.5 h / 25 °C
View Scheme

: 20455-07-6
p-nitrophenyl methanesulfonate

: 130288-24-3
(+)-duocarmycin SA

Conditions

Conditions	Yield
Multi-step reaction with 26 steps 1.1: 100 percent / H2 / Ra-Ni / ethyl acetate; ethanol / 24 h / 23 °C / 72400.7 Torr 2.1: 94.5 g / Br2 / methanol; CH2Cl2 / 0.5 h / 0 - 23 °C 3.1: aq. NaNO2; H2SO4 / acetonitrile / 0 °C 3.2: 96 percent / aq. KI / acetonitrile / 0.75 h 4.1: 100 percent / KOH / CH2Cl2; methanol / 0.08 h / 23 °C 5.1: 88 percent / K2CO3 / dimethylformamide / 1 h / 23 °C 6.1: n-BuLi / toluene; hexane / -78 °C 6.2: 4.18 g / toluene 7.1: aq. acetic acid / 3 h / 100 °C 8.1: H5IO6 / tetrahydrofuran / 0.08 h / 0 °C 9.1: 2.76 percent / NaBH4 / methanol / 0.08 h / -78 °C 10.1: aq. HCl; Fe; FeCl2 / ethanol / 2 h / Heating 11.1: 3.42 percent / aq. NaHCO3 / CH2Cl2 / 0.08 h / 23 °C 12.1: K2CO3 / dimethylformamide / 1 h / 23 °C 13.1: 1.91 g / PhSH / dimethylformamide / 1 h / 23 °C 14.1: 67 percent / CuI; CsOAc / dimethylsulfoxide / 24 h / 23 °C 15.1: 100 percent / imidazole / dimethylformamide / 0.17 h / 23 °C 16.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 16.2: 97 percent / I2 / tetrahydrofuran; hexane / 0.33 h / -78 °C 17.1: 72 percent / PdCl2; P(o-tolyl)3; Et3N / acetonitrile / 4 h / 90 °C / Heating 18.1: 82 percent / NBS / dimethylformamide / 0.08 h / 23 °C 19.1: 100 percent / CuI; CsOAc / dimethylsulfoxide / 0.17 h / 23 °C 20.1: 77 percent / NaHCO3 / acetonitrile / 0.33 h / 70 °C 21.1: 58 percent / Zn; aq. KH2PO4 / tetrahydrofuran / 1 h / 23 °C 22.1: 83 percent / pyridine; CH2Cl2 / 0.17 h / 0 °C 23.1: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 23 °C 24.1: 88 percent / pyridine / 0.17 h / 23 °C 25.1: 81 percent / H2 / Pd/C / ethanol; ethyl acetate / 0.17 h / 23 °C 26.1: 92 percent / Cs2CO3 / acetonitrile / 1 h / 23 °C View Scheme

Yield

Multi-step reaction with 26 steps
1.1: 100 percent / H2 / Ra-Ni / ethyl acetate; ethanol / 24 h / 23 °C / 72400.7 Torr
2.1: 94.5 g / Br2 / methanol; CH2Cl2 / 0.5 h / 0 - 23 °C
3.1: aq. NaNO2; H2SO4 / acetonitrile / 0 °C
3.2: 96 percent / aq. KI / acetonitrile / 0.75 h
4.1: 100 percent / KOH / CH2Cl2; methanol / 0.08 h / 23 °C
5.1: 88 percent / K2CO3 / dimethylformamide / 1 h / 23 °C
6.1: n-BuLi / toluene; hexane / -78 °C
6.2: 4.18 g / toluene
7.1: aq. acetic acid / 3 h / 100 °C
8.1: H5IO6 / tetrahydrofuran / 0.08 h / 0 °C
9.1: 2.76 percent / NaBH4 / methanol / 0.08 h / -78 °C
10.1: aq. HCl; Fe; FeCl2 / ethanol / 2 h / Heating
11.1: 3.42 percent / aq. NaHCO3 / CH2Cl2 / 0.08 h / 23 °C
12.1: K2CO3 / dimethylformamide / 1 h / 23 °C
13.1: 1.91 g / PhSH / dimethylformamide / 1 h / 23 °C
14.1: 67 percent / CuI; CsOAc / dimethylsulfoxide / 24 h / 23 °C
15.1: 100 percent / imidazole / dimethylformamide / 0.17 h / 23 °C
16.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
16.2: 97 percent / I2 / tetrahydrofuran; hexane / 0.33 h / -78 °C
17.1: 72 percent / PdCl2; P(o-tolyl)3; Et3N / acetonitrile / 4 h / 90 °C / Heating
18.1: 82 percent / NBS / dimethylformamide / 0.08 h / 23 °C
19.1: 100 percent / CuI; CsOAc / dimethylsulfoxide / 0.17 h / 23 °C
20.1: 77 percent / NaHCO3 / acetonitrile / 0.33 h / 70 °C
21.1: 58 percent / Zn; aq. KH2PO4 / tetrahydrofuran / 1 h / 23 °C
22.1: 83 percent / pyridine; CH2Cl2 / 0.17 h / 0 °C
23.1: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 23 °C
24.1: 88 percent / pyridine / 0.17 h / 23 °C
25.1: 81 percent / H2 / Pd/C / ethanol; ethyl acetate / 0.17 h / 23 °C
26.1: 92 percent / Cs2CO3 / acetonitrile / 1 h / 23 °C
View Scheme

: 24690-19-5
methanesulfonic acid 4-aminophenyl ester

: 130288-24-3
(+)-duocarmycin SA

Conditions

Conditions	Yield
Multi-step reaction with 25 steps 1.1: 94.5 g / Br2 / methanol; CH2Cl2 / 0.5 h / 0 - 23 °C 2.1: aq. NaNO2; H2SO4 / acetonitrile / 0 °C 2.2: 96 percent / aq. KI / acetonitrile / 0.75 h 3.1: 100 percent / KOH / CH2Cl2; methanol / 0.08 h / 23 °C 4.1: 88 percent / K2CO3 / dimethylformamide / 1 h / 23 °C 5.1: n-BuLi / toluene; hexane / -78 °C 5.2: 4.18 g / toluene 6.1: aq. acetic acid / 3 h / 100 °C 7.1: H5IO6 / tetrahydrofuran / 0.08 h / 0 °C 8.1: 2.76 percent / NaBH4 / methanol / 0.08 h / -78 °C 9.1: aq. HCl; Fe; FeCl2 / ethanol / 2 h / Heating 10.1: 3.42 percent / aq. NaHCO3 / CH2Cl2 / 0.08 h / 23 °C 11.1: K2CO3 / dimethylformamide / 1 h / 23 °C 12.1: 1.91 g / PhSH / dimethylformamide / 1 h / 23 °C 13.1: 67 percent / CuI; CsOAc / dimethylsulfoxide / 24 h / 23 °C 14.1: 100 percent / imidazole / dimethylformamide / 0.17 h / 23 °C 15.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 15.2: 97 percent / I2 / tetrahydrofuran; hexane / 0.33 h / -78 °C 16.1: 72 percent / PdCl2; P(o-tolyl)3; Et3N / acetonitrile / 4 h / 90 °C / Heating 17.1: 82 percent / NBS / dimethylformamide / 0.08 h / 23 °C 18.1: 100 percent / CuI; CsOAc / dimethylsulfoxide / 0.17 h / 23 °C 19.1: 77 percent / NaHCO3 / acetonitrile / 0.33 h / 70 °C 20.1: 58 percent / Zn; aq. KH2PO4 / tetrahydrofuran / 1 h / 23 °C 21.1: 83 percent / pyridine; CH2Cl2 / 0.17 h / 0 °C 22.1: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 23 °C 23.1: 88 percent / pyridine / 0.17 h / 23 °C 24.1: 81 percent / H2 / Pd/C / ethanol; ethyl acetate / 0.17 h / 23 °C 25.1: 92 percent / Cs2CO3 / acetonitrile / 1 h / 23 °C View Scheme

Yield

Multi-step reaction with 25 steps
1.1: 94.5 g / Br2 / methanol; CH2Cl2 / 0.5 h / 0 - 23 °C
2.1: aq. NaNO2; H2SO4 / acetonitrile / 0 °C
2.2: 96 percent / aq. KI / acetonitrile / 0.75 h
3.1: 100 percent / KOH / CH2Cl2; methanol / 0.08 h / 23 °C
4.1: 88 percent / K2CO3 / dimethylformamide / 1 h / 23 °C
5.1: n-BuLi / toluene; hexane / -78 °C
5.2: 4.18 g / toluene
6.1: aq. acetic acid / 3 h / 100 °C
7.1: H5IO6 / tetrahydrofuran / 0.08 h / 0 °C
8.1: 2.76 percent / NaBH4 / methanol / 0.08 h / -78 °C
9.1: aq. HCl; Fe; FeCl2 / ethanol / 2 h / Heating
10.1: 3.42 percent / aq. NaHCO3 / CH2Cl2 / 0.08 h / 23 °C
11.1: K2CO3 / dimethylformamide / 1 h / 23 °C
12.1: 1.91 g / PhSH / dimethylformamide / 1 h / 23 °C
13.1: 67 percent / CuI; CsOAc / dimethylsulfoxide / 24 h / 23 °C
14.1: 100 percent / imidazole / dimethylformamide / 0.17 h / 23 °C
15.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
15.2: 97 percent / I2 / tetrahydrofuran; hexane / 0.33 h / -78 °C
16.1: 72 percent / PdCl2; P(o-tolyl)3; Et3N / acetonitrile / 4 h / 90 °C / Heating
17.1: 82 percent / NBS / dimethylformamide / 0.08 h / 23 °C
18.1: 100 percent / CuI; CsOAc / dimethylsulfoxide / 0.17 h / 23 °C
19.1: 77 percent / NaHCO3 / acetonitrile / 0.33 h / 70 °C
20.1: 58 percent / Zn; aq. KH2PO4 / tetrahydrofuran / 1 h / 23 °C
21.1: 83 percent / pyridine; CH2Cl2 / 0.17 h / 0 °C
22.1: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 23 °C
23.1: 88 percent / pyridine / 0.17 h / 23 °C
24.1: 81 percent / H2 / Pd/C / ethanol; ethyl acetate / 0.17 h / 23 °C
25.1: 92 percent / Cs2CO3 / acetonitrile / 1 h / 23 °C
View Scheme

: 35274-53-4
2-bromo-3,4,5-tri-methoxybenzaldehyde

: 130288-24-3
(+)-duocarmycin SA

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: 97 percent / 1,1,3,3-tetramethylguanidine / CH2Cl2 / 48 h / 23 °C 2: 98 percent / CuI; CsOAc / dimethylsulfoxide / 24 h / 23 °C 3: 99 percent / H2 / Pd/C / ethyl acetate; ethanol / 3 h / 23 °C 4: 89 percent / aq. KOH / methanol / 1 h / Heating 5: SOCl2; DMF / toluene / 0.33 h / 70 °C 6: 83 percent / pyridine; CH2Cl2 / 0.17 h / 0 °C 7: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 23 °C 8: 88 percent / pyridine / 0.17 h / 23 °C 9: 81 percent / H2 / Pd/C / ethanol; ethyl acetate / 0.17 h / 23 °C 10: 92 percent / Cs2CO3 / acetonitrile / 1 h / 23 °C View Scheme
Multi-step reaction with 9 steps 1.1: potassium acetate / tetrahydrofuran / 2 h / 60 °C / Inert atmosphere 2.1: triethylamine / methanol / 0.5 h / 60 °C 3.1: 1,10-Phenanthroline; potassium carbonate; copper(l) iodide / N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere 4.1: water; tetrahydrofuran / 3 h / 60 °C / Inert atmosphere 5.1: oxalyl dichloride / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / Inert atmosphere 5.2: Reflux 6.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 2.2 °C / Inert atmosphere 7.1: 10 wt% Pd(OH)2 on carbon; hydrogen; ammonium formate / methanol / 1 h / 35 - 50 °C / Inert atmosphere 8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 35 °C / Inert atmosphere 9.1: tributylphosphine; azodicarbonyl dimorpholide / tetrahydrofuran / 2 h / Inert atmosphere View Scheme

Yield

Multi-step reaction with 10 steps
1: 97 percent / 1,1,3,3-tetramethylguanidine / CH2Cl2 / 48 h / 23 °C
2: 98 percent / CuI; CsOAc / dimethylsulfoxide / 24 h / 23 °C
3: 99 percent / H2 / Pd/C / ethyl acetate; ethanol / 3 h / 23 °C
4: 89 percent / aq. KOH / methanol / 1 h / Heating
5: SOCl2; DMF / toluene / 0.33 h / 70 °C
6: 83 percent / pyridine; CH2Cl2 / 0.17 h / 0 °C
7: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 23 °C
8: 88 percent / pyridine / 0.17 h / 23 °C
9: 81 percent / H2 / Pd/C / ethanol; ethyl acetate / 0.17 h / 23 °C
10: 92 percent / Cs2CO3 / acetonitrile / 1 h / 23 °C
View Scheme

Multi-step reaction with 9 steps
1.1: potassium acetate / tetrahydrofuran / 2 h / 60 °C / Inert atmosphere
2.1: triethylamine / methanol / 0.5 h / 60 °C
3.1: 1,10-Phenanthroline; potassium carbonate; copper(l) iodide / N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere
4.1: water; tetrahydrofuran / 3 h / 60 °C / Inert atmosphere
5.1: oxalyl dichloride / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / Inert atmosphere
5.2: Reflux
6.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 2.2 °C / Inert atmosphere
7.1: 10 wt% Pd(OH)2 on carbon; hydrogen; ammonium formate / methanol / 1 h / 35 - 50 °C / Inert atmosphere
8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 35 °C / Inert atmosphere
9.1: tributylphosphine; azodicarbonyl dimorpholide / tetrahydrofuran / 2 h / Inert atmosphere
View Scheme

: 128781-07-7
5,6,7-trimethoxy-1H-indole-2-carboxylic acid

: 130288-24-3
(+)-duocarmycin SA

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: SOCl2; DMF / toluene / 0.33 h / 70 °C 2: 83 percent / pyridine; CH2Cl2 / 0.17 h / 0 °C 3: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 23 °C 4: 88 percent / pyridine / 0.17 h / 23 °C 5: 81 percent / H2 / Pd/C / ethanol; ethyl acetate / 0.17 h / 23 °C 6: 92 percent / Cs2CO3 / acetonitrile / 1 h / 23 °C View Scheme
Multi-step reaction with 2 steps 1: EDCI, NaHCO3 / dimethylformamide / 15 h / 25 °C 2: 87 percent / NaH / tetrahydrofuran; dimethylformamide / 0.5 h / 0 °C View Scheme
Multi-step reaction with 5 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / Inert atmosphere 1.2: Reflux 2.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 2.2 °C / Inert atmosphere 3.1: 10 wt% Pd(OH)2 on carbon; hydrogen; ammonium formate / methanol / 1 h / 35 - 50 °C / Inert atmosphere 4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 35 °C / Inert atmosphere 5.1: tributylphosphine; azodicarbonyl dimorpholide / tetrahydrofuran / 2 h / Inert atmosphere View Scheme
Multi-step reaction with 6 steps 1.1: oxalyl dichloride; N,N-dimethyl-formamide / tetrahydrofuran / 0.5 h 2.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h 3.1: zinc; acetic acid / acetonitrile / 72 h 4.1: magnesium sulfate / dichloromethane / 23 h 4.2: 4 h / 50 °C 5.1: 20% palladium hydroxide-activated charcoal; ammonium formate; methanol / water / 50 °C / Inert atmosphere 5.2: 3 h / 35 °C / Inert atmosphere 6.1: tributylphosphine; 1,1'-azodicarbonyl-dipiperidine / tetrahydrofuran / 0.33 h / Inert atmosphere View Scheme

: 118292-37-8
5,6,7-trimethoxy-1H-indole-2-carboxylic acid methyl ester

: 130288-24-3
(+)-duocarmycin SA

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 89 percent / aq. KOH / methanol / 1 h / Heating 2: SOCl2; DMF / toluene / 0.33 h / 70 °C 3: 83 percent / pyridine; CH2Cl2 / 0.17 h / 0 °C 4: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 23 °C 5: 88 percent / pyridine / 0.17 h / 23 °C 6: 81 percent / H2 / Pd/C / ethanol; ethyl acetate / 0.17 h / 23 °C 7: 92 percent / Cs2CO3 / acetonitrile / 1 h / 23 °C View Scheme

Yield

Multi-step reaction with 7 steps
1: 89 percent / aq. KOH / methanol / 1 h / Heating
2: SOCl2; DMF / toluene / 0.33 h / 70 °C
3: 83 percent / pyridine; CH2Cl2 / 0.17 h / 0 °C
4: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 23 °C
5: 88 percent / pyridine / 0.17 h / 23 °C
6: 81 percent / H2 / Pd/C / ethanol; ethyl acetate / 0.17 h / 23 °C
7: 92 percent / Cs2CO3 / acetonitrile / 1 h / 23 °C
View Scheme

: 86-81-7
3,4,5-trimethoxy-benzaldehyde

: 130288-24-3
(+)-duocarmycin SA

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1: 87 percent / Br2; AcOH / CH2Cl2 / 0.5 h / 0 °C 2: 97 percent / 1,1,3,3-tetramethylguanidine / CH2Cl2 / 48 h / 23 °C 3: 98 percent / CuI; CsOAc / dimethylsulfoxide / 24 h / 23 °C 4: 99 percent / H2 / Pd/C / ethyl acetate; ethanol / 3 h / 23 °C 5: 89 percent / aq. KOH / methanol / 1 h / Heating 6: SOCl2; DMF / toluene / 0.33 h / 70 °C 7: 83 percent / pyridine; CH2Cl2 / 0.17 h / 0 °C 8: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 23 °C 9: 88 percent / pyridine / 0.17 h / 23 °C 10: 81 percent / H2 / Pd/C / ethanol; ethyl acetate / 0.17 h / 23 °C 11: 92 percent / Cs2CO3 / acetonitrile / 1 h / 23 °C View Scheme
Multi-step reaction with 10 steps 1.1: N-Bromosuccinimide / acetonitrile / 1 h / 50 °C / Inert atmosphere 2.1: potassium acetate / tetrahydrofuran / 2 h / 60 °C / Inert atmosphere 3.1: triethylamine / methanol / 0.5 h / 60 °C 4.1: 1,10-Phenanthroline; potassium carbonate; copper(l) iodide / N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere 5.1: water; tetrahydrofuran / 3 h / 60 °C / Inert atmosphere 6.1: oxalyl dichloride / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / Inert atmosphere 6.2: Reflux 7.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 2.2 °C / Inert atmosphere 8.1: 10 wt% Pd(OH)2 on carbon; hydrogen; ammonium formate / methanol / 1 h / 35 - 50 °C / Inert atmosphere 9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 35 °C / Inert atmosphere 10.1: tributylphosphine; azodicarbonyl dimorpholide / tetrahydrofuran / 2 h / Inert atmosphere View Scheme

Yield

Multi-step reaction with 11 steps
1: 87 percent / Br2; AcOH / CH2Cl2 / 0.5 h / 0 °C
2: 97 percent / 1,1,3,3-tetramethylguanidine / CH2Cl2 / 48 h / 23 °C
3: 98 percent / CuI; CsOAc / dimethylsulfoxide / 24 h / 23 °C
4: 99 percent / H2 / Pd/C / ethyl acetate; ethanol / 3 h / 23 °C
5: 89 percent / aq. KOH / methanol / 1 h / Heating
6: SOCl2; DMF / toluene / 0.33 h / 70 °C
7: 83 percent / pyridine; CH2Cl2 / 0.17 h / 0 °C
8: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 23 °C
9: 88 percent / pyridine / 0.17 h / 23 °C
10: 81 percent / H2 / Pd/C / ethanol; ethyl acetate / 0.17 h / 23 °C
11: 92 percent / Cs2CO3 / acetonitrile / 1 h / 23 °C
View Scheme

Multi-step reaction with 10 steps
1.1: N-Bromosuccinimide / acetonitrile / 1 h / 50 °C / Inert atmosphere
2.1: potassium acetate / tetrahydrofuran / 2 h / 60 °C / Inert atmosphere
3.1: triethylamine / methanol / 0.5 h / 60 °C
4.1: 1,10-Phenanthroline; potassium carbonate; copper(l) iodide / N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere
5.1: water; tetrahydrofuran / 3 h / 60 °C / Inert atmosphere
6.1: oxalyl dichloride / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / Inert atmosphere
6.2: Reflux
7.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 2.2 °C / Inert atmosphere
8.1: 10 wt% Pd(OH)2 on carbon; hydrogen; ammonium formate / methanol / 1 h / 35 - 50 °C / Inert atmosphere
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 35 °C / Inert atmosphere
10.1: tributylphosphine; azodicarbonyl dimorpholide / tetrahydrofuran / 2 h / Inert atmosphere
View Scheme

: 556038-75-6
3,5-dibromo-4-iodophenyjl

: 130288-24-3
(+)-duocarmycin SA

Conditions

Conditions	Yield
Multi-step reaction with 22 steps 1.1: 88 percent / K2CO3 / dimethylformamide / 1 h / 23 °C 2.1: n-BuLi / toluene; hexane / -78 °C 2.2: 4.18 g / toluene 3.1: aq. acetic acid / 3 h / 100 °C 4.1: H5IO6 / tetrahydrofuran / 0.08 h / 0 °C 5.1: 2.76 percent / NaBH4 / methanol / 0.08 h / -78 °C 6.1: aq. HCl; Fe; FeCl2 / ethanol / 2 h / Heating 7.1: 3.42 percent / aq. NaHCO3 / CH2Cl2 / 0.08 h / 23 °C 8.1: K2CO3 / dimethylformamide / 1 h / 23 °C 9.1: 1.91 g / PhSH / dimethylformamide / 1 h / 23 °C 10.1: 67 percent / CuI; CsOAc / dimethylsulfoxide / 24 h / 23 °C 11.1: 100 percent / imidazole / dimethylformamide / 0.17 h / 23 °C 12.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 12.2: 97 percent / I2 / tetrahydrofuran; hexane / 0.33 h / -78 °C 13.1: 72 percent / PdCl2; P(o-tolyl)3; Et3N / acetonitrile / 4 h / 90 °C / Heating 14.1: 82 percent / NBS / dimethylformamide / 0.08 h / 23 °C 15.1: 100 percent / CuI; CsOAc / dimethylsulfoxide / 0.17 h / 23 °C 16.1: 77 percent / NaHCO3 / acetonitrile / 0.33 h / 70 °C 17.1: 58 percent / Zn; aq. KH2PO4 / tetrahydrofuran / 1 h / 23 °C 18.1: 83 percent / pyridine; CH2Cl2 / 0.17 h / 0 °C 19.1: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 23 °C 20.1: 88 percent / pyridine / 0.17 h / 23 °C 21.1: 81 percent / H2 / Pd/C / ethanol; ethyl acetate / 0.17 h / 23 °C 22.1: 92 percent / Cs2CO3 / acetonitrile / 1 h / 23 °C View Scheme

Yield

Multi-step reaction with 22 steps
1.1: 88 percent / K2CO3 / dimethylformamide / 1 h / 23 °C
2.1: n-BuLi / toluene; hexane / -78 °C
2.2: 4.18 g / toluene
3.1: aq. acetic acid / 3 h / 100 °C
4.1: H5IO6 / tetrahydrofuran / 0.08 h / 0 °C
5.1: 2.76 percent / NaBH4 / methanol / 0.08 h / -78 °C
6.1: aq. HCl; Fe; FeCl2 / ethanol / 2 h / Heating
7.1: 3.42 percent / aq. NaHCO3 / CH2Cl2 / 0.08 h / 23 °C
8.1: K2CO3 / dimethylformamide / 1 h / 23 °C
9.1: 1.91 g / PhSH / dimethylformamide / 1 h / 23 °C
10.1: 67 percent / CuI; CsOAc / dimethylsulfoxide / 24 h / 23 °C
11.1: 100 percent / imidazole / dimethylformamide / 0.17 h / 23 °C
12.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
12.2: 97 percent / I2 / tetrahydrofuran; hexane / 0.33 h / -78 °C
13.1: 72 percent / PdCl2; P(o-tolyl)3; Et3N / acetonitrile / 4 h / 90 °C / Heating
14.1: 82 percent / NBS / dimethylformamide / 0.08 h / 23 °C
15.1: 100 percent / CuI; CsOAc / dimethylsulfoxide / 0.17 h / 23 °C
16.1: 77 percent / NaHCO3 / acetonitrile / 0.33 h / 70 °C
17.1: 58 percent / Zn; aq. KH2PO4 / tetrahydrofuran / 1 h / 23 °C
18.1: 83 percent / pyridine; CH2Cl2 / 0.17 h / 0 °C
19.1: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 23 °C
20.1: 88 percent / pyridine / 0.17 h / 23 °C
21.1: 81 percent / H2 / Pd/C / ethanol; ethyl acetate / 0.17 h / 23 °C
22.1: 92 percent / Cs2CO3 / acetonitrile / 1 h / 23 °C
View Scheme

: 556038-73-4
methanesulfonic acid 4-amino-3,5-dibromophenyl ester

: 130288-24-3
(+)-duocarmycin SA

Conditions

Conditions	Yield
Multi-step reaction with 24 steps 1.1: aq. NaNO2; H2SO4 / acetonitrile / 0 °C 1.2: 96 percent / aq. KI / acetonitrile / 0.75 h 2.1: 100 percent / KOH / CH2Cl2; methanol / 0.08 h / 23 °C 3.1: 88 percent / K2CO3 / dimethylformamide / 1 h / 23 °C 4.1: n-BuLi / toluene; hexane / -78 °C 4.2: 4.18 g / toluene 5.1: aq. acetic acid / 3 h / 100 °C 6.1: H5IO6 / tetrahydrofuran / 0.08 h / 0 °C 7.1: 2.76 percent / NaBH4 / methanol / 0.08 h / -78 °C 8.1: aq. HCl; Fe; FeCl2 / ethanol / 2 h / Heating 9.1: 3.42 percent / aq. NaHCO3 / CH2Cl2 / 0.08 h / 23 °C 10.1: K2CO3 / dimethylformamide / 1 h / 23 °C 11.1: 1.91 g / PhSH / dimethylformamide / 1 h / 23 °C 12.1: 67 percent / CuI; CsOAc / dimethylsulfoxide / 24 h / 23 °C 13.1: 100 percent / imidazole / dimethylformamide / 0.17 h / 23 °C 14.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 14.2: 97 percent / I2 / tetrahydrofuran; hexane / 0.33 h / -78 °C 15.1: 72 percent / PdCl2; P(o-tolyl)3; Et3N / acetonitrile / 4 h / 90 °C / Heating 16.1: 82 percent / NBS / dimethylformamide / 0.08 h / 23 °C 17.1: 100 percent / CuI; CsOAc / dimethylsulfoxide / 0.17 h / 23 °C 18.1: 77 percent / NaHCO3 / acetonitrile / 0.33 h / 70 °C 19.1: 58 percent / Zn; aq. KH2PO4 / tetrahydrofuran / 1 h / 23 °C 20.1: 83 percent / pyridine; CH2Cl2 / 0.17 h / 0 °C 21.1: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 23 °C 22.1: 88 percent / pyridine / 0.17 h / 23 °C 23.1: 81 percent / H2 / Pd/C / ethanol; ethyl acetate / 0.17 h / 23 °C 24.1: 92 percent / Cs2CO3 / acetonitrile / 1 h / 23 °C View Scheme

Yield

Multi-step reaction with 24 steps
1.1: aq. NaNO2; H2SO4 / acetonitrile / 0 °C
1.2: 96 percent / aq. KI / acetonitrile / 0.75 h
2.1: 100 percent / KOH / CH2Cl2; methanol / 0.08 h / 23 °C
3.1: 88 percent / K2CO3 / dimethylformamide / 1 h / 23 °C
4.1: n-BuLi / toluene; hexane / -78 °C
4.2: 4.18 g / toluene
5.1: aq. acetic acid / 3 h / 100 °C
6.1: H5IO6 / tetrahydrofuran / 0.08 h / 0 °C
7.1: 2.76 percent / NaBH4 / methanol / 0.08 h / -78 °C
8.1: aq. HCl; Fe; FeCl2 / ethanol / 2 h / Heating
9.1: 3.42 percent / aq. NaHCO3 / CH2Cl2 / 0.08 h / 23 °C
10.1: K2CO3 / dimethylformamide / 1 h / 23 °C
11.1: 1.91 g / PhSH / dimethylformamide / 1 h / 23 °C
12.1: 67 percent / CuI; CsOAc / dimethylsulfoxide / 24 h / 23 °C
13.1: 100 percent / imidazole / dimethylformamide / 0.17 h / 23 °C
14.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
14.2: 97 percent / I2 / tetrahydrofuran; hexane / 0.33 h / -78 °C
15.1: 72 percent / PdCl2; P(o-tolyl)3; Et3N / acetonitrile / 4 h / 90 °C / Heating
16.1: 82 percent / NBS / dimethylformamide / 0.08 h / 23 °C
17.1: 100 percent / CuI; CsOAc / dimethylsulfoxide / 0.17 h / 23 °C
18.1: 77 percent / NaHCO3 / acetonitrile / 0.33 h / 70 °C
19.1: 58 percent / Zn; aq. KH2PO4 / tetrahydrofuran / 1 h / 23 °C
20.1: 83 percent / pyridine; CH2Cl2 / 0.17 h / 0 °C
21.1: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 23 °C
22.1: 88 percent / pyridine / 0.17 h / 23 °C
23.1: 81 percent / H2 / Pd/C / ethanol; ethyl acetate / 0.17 h / 23 °C
24.1: 92 percent / Cs2CO3 / acetonitrile / 1 h / 23 °C
View Scheme

: 556038-74-5
methanesulfonic acid 3,5-dibromo-4-iodophenyl ester

: 130288-24-3
(+)-duocarmycin SA

Conditions

Conditions	Yield
Multi-step reaction with 23 steps 1.1: 100 percent / KOH / CH2Cl2; methanol / 0.08 h / 23 °C 2.1: 88 percent / K2CO3 / dimethylformamide / 1 h / 23 °C 3.1: n-BuLi / toluene; hexane / -78 °C 3.2: 4.18 g / toluene 4.1: aq. acetic acid / 3 h / 100 °C 5.1: H5IO6 / tetrahydrofuran / 0.08 h / 0 °C 6.1: 2.76 percent / NaBH4 / methanol / 0.08 h / -78 °C 7.1: aq. HCl; Fe; FeCl2 / ethanol / 2 h / Heating 8.1: 3.42 percent / aq. NaHCO3 / CH2Cl2 / 0.08 h / 23 °C 9.1: K2CO3 / dimethylformamide / 1 h / 23 °C 10.1: 1.91 g / PhSH / dimethylformamide / 1 h / 23 °C 11.1: 67 percent / CuI; CsOAc / dimethylsulfoxide / 24 h / 23 °C 12.1: 100 percent / imidazole / dimethylformamide / 0.17 h / 23 °C 13.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 13.2: 97 percent / I2 / tetrahydrofuran; hexane / 0.33 h / -78 °C 14.1: 72 percent / PdCl2; P(o-tolyl)3; Et3N / acetonitrile / 4 h / 90 °C / Heating 15.1: 82 percent / NBS / dimethylformamide / 0.08 h / 23 °C 16.1: 100 percent / CuI; CsOAc / dimethylsulfoxide / 0.17 h / 23 °C 17.1: 77 percent / NaHCO3 / acetonitrile / 0.33 h / 70 °C 18.1: 58 percent / Zn; aq. KH2PO4 / tetrahydrofuran / 1 h / 23 °C 19.1: 83 percent / pyridine; CH2Cl2 / 0.17 h / 0 °C 20.1: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 23 °C 21.1: 88 percent / pyridine / 0.17 h / 23 °C 22.1: 81 percent / H2 / Pd/C / ethanol; ethyl acetate / 0.17 h / 23 °C 23.1: 92 percent / Cs2CO3 / acetonitrile / 1 h / 23 °C View Scheme

Yield

Multi-step reaction with 23 steps
1.1: 100 percent / KOH / CH2Cl2; methanol / 0.08 h / 23 °C
2.1: 88 percent / K2CO3 / dimethylformamide / 1 h / 23 °C
3.1: n-BuLi / toluene; hexane / -78 °C
3.2: 4.18 g / toluene
4.1: aq. acetic acid / 3 h / 100 °C
5.1: H5IO6 / tetrahydrofuran / 0.08 h / 0 °C
6.1: 2.76 percent / NaBH4 / methanol / 0.08 h / -78 °C
7.1: aq. HCl; Fe; FeCl2 / ethanol / 2 h / Heating
8.1: 3.42 percent / aq. NaHCO3 / CH2Cl2 / 0.08 h / 23 °C
9.1: K2CO3 / dimethylformamide / 1 h / 23 °C
10.1: 1.91 g / PhSH / dimethylformamide / 1 h / 23 °C
11.1: 67 percent / CuI; CsOAc / dimethylsulfoxide / 24 h / 23 °C
12.1: 100 percent / imidazole / dimethylformamide / 0.17 h / 23 °C
13.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
13.2: 97 percent / I2 / tetrahydrofuran; hexane / 0.33 h / -78 °C
14.1: 72 percent / PdCl2; P(o-tolyl)3; Et3N / acetonitrile / 4 h / 90 °C / Heating
15.1: 82 percent / NBS / dimethylformamide / 0.08 h / 23 °C
16.1: 100 percent / CuI; CsOAc / dimethylsulfoxide / 0.17 h / 23 °C
17.1: 77 percent / NaHCO3 / acetonitrile / 0.33 h / 70 °C
18.1: 58 percent / Zn; aq. KH2PO4 / tetrahydrofuran / 1 h / 23 °C
19.1: 83 percent / pyridine; CH2Cl2 / 0.17 h / 0 °C
20.1: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 23 °C
21.1: 88 percent / pyridine / 0.17 h / 23 °C
22.1: 81 percent / H2 / Pd/C / ethanol; ethyl acetate / 0.17 h / 23 °C
23.1: 92 percent / Cs2CO3 / acetonitrile / 1 h / 23 °C
View Scheme

: 556038-43-8
3,5-dibromo-4-iodophenol benzyl ether

: 130288-24-3
(+)-duocarmycin SA

Conditions

Conditions	Yield
Multi-step reaction with 21 steps 1.1: n-BuLi / toluene; hexane / -78 °C 1.2: 4.18 g / toluene 2.1: aq. acetic acid / 3 h / 100 °C 3.1: H5IO6 / tetrahydrofuran / 0.08 h / 0 °C 4.1: 2.76 percent / NaBH4 / methanol / 0.08 h / -78 °C 5.1: aq. HCl; Fe; FeCl2 / ethanol / 2 h / Heating 6.1: 3.42 percent / aq. NaHCO3 / CH2Cl2 / 0.08 h / 23 °C 7.1: K2CO3 / dimethylformamide / 1 h / 23 °C 8.1: 1.91 g / PhSH / dimethylformamide / 1 h / 23 °C 9.1: 67 percent / CuI; CsOAc / dimethylsulfoxide / 24 h / 23 °C 10.1: 100 percent / imidazole / dimethylformamide / 0.17 h / 23 °C 11.1: n-BuLi / tetrahydrofuran; hexane / -78 °C 11.2: 97 percent / I2 / tetrahydrofuran; hexane / 0.33 h / -78 °C 12.1: 72 percent / PdCl2; P(o-tolyl)3; Et3N / acetonitrile / 4 h / 90 °C / Heating 13.1: 82 percent / NBS / dimethylformamide / 0.08 h / 23 °C 14.1: 100 percent / CuI; CsOAc / dimethylsulfoxide / 0.17 h / 23 °C 15.1: 77 percent / NaHCO3 / acetonitrile / 0.33 h / 70 °C 16.1: 58 percent / Zn; aq. KH2PO4 / tetrahydrofuran / 1 h / 23 °C 17.1: 83 percent / pyridine; CH2Cl2 / 0.17 h / 0 °C 18.1: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 23 °C 19.1: 88 percent / pyridine / 0.17 h / 23 °C 20.1: 81 percent / H2 / Pd/C / ethanol; ethyl acetate / 0.17 h / 23 °C 21.1: 92 percent / Cs2CO3 / acetonitrile / 1 h / 23 °C View Scheme

Yield

Multi-step reaction with 21 steps
1.1: n-BuLi / toluene; hexane / -78 °C
1.2: 4.18 g / toluene
2.1: aq. acetic acid / 3 h / 100 °C
3.1: H5IO6 / tetrahydrofuran / 0.08 h / 0 °C
4.1: 2.76 percent / NaBH4 / methanol / 0.08 h / -78 °C
5.1: aq. HCl; Fe; FeCl2 / ethanol / 2 h / Heating
6.1: 3.42 percent / aq. NaHCO3 / CH2Cl2 / 0.08 h / 23 °C
7.1: K2CO3 / dimethylformamide / 1 h / 23 °C
8.1: 1.91 g / PhSH / dimethylformamide / 1 h / 23 °C
9.1: 67 percent / CuI; CsOAc / dimethylsulfoxide / 24 h / 23 °C
10.1: 100 percent / imidazole / dimethylformamide / 0.17 h / 23 °C
11.1: n-BuLi / tetrahydrofuran; hexane / -78 °C
11.2: 97 percent / I2 / tetrahydrofuran; hexane / 0.33 h / -78 °C
12.1: 72 percent / PdCl2; P(o-tolyl)3; Et3N / acetonitrile / 4 h / 90 °C / Heating
13.1: 82 percent / NBS / dimethylformamide / 0.08 h / 23 °C
14.1: 100 percent / CuI; CsOAc / dimethylsulfoxide / 0.17 h / 23 °C
15.1: 77 percent / NaHCO3 / acetonitrile / 0.33 h / 70 °C
16.1: 58 percent / Zn; aq. KH2PO4 / tetrahydrofuran / 1 h / 23 °C
17.1: 83 percent / pyridine; CH2Cl2 / 0.17 h / 0 °C
18.1: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 23 °C
19.1: 88 percent / pyridine / 0.17 h / 23 °C
20.1: 81 percent / H2 / Pd/C / ethanol; ethyl acetate / 0.17 h / 23 °C
21.1: 92 percent / Cs2CO3 / acetonitrile / 1 h / 23 °C
View Scheme

: 130288-24-3
(+)-duocarmycin SA

: 150992-82-8
(+)-(7bR,8aS)-methyl 4-oxo-1,2,4,5,8,8a-hexahydrocyclopropapyrrolo<3,2-e>indole-6-carboxylate

Conditions

Conditions	Yield
With sodium methylate In methanol; acetonitrile for 1h; Ambient temperature;	99%

: 130288-24-3
(+)-duocarmycin SA

: 144667-38-9
duocarmycin

Conditions

Conditions	Yield
With hydrogenchloride In ethyl acetate at 0℃; for 0.25h;	96%

: 130288-24-3
(+)-duocarmycin SA

calf thymus DNA: calf thymus DNA

: (+)-duocarmycin SA-adenine adduct

Conditions

Conditions	Yield
With potassium phosphate buffer In N,N-dimethyl-formamide at 37℃; for 24h;	81%
With sodium phosphate buffer 1.) 25 deg C, 24 h, 2.) 100 deg C, 25 min; Yield given. Multistep reaction;

: 130288-24-3
(+)-duocarmycin SA

: (S)-8-Chloromethyl-4-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-3,4,6,7,8,8a-hexahydro-pyrrolo[3,2-e]indole-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
With hydrogenchloride In acetonitrile for 1h; Ambient temperature;

: 130288-24-3
(+)-duocarmycin SA

: (S)-8-Bromomethyl-4-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-3,4,6,7,8,8a-hexahydro-pyrrolo[3,2-e]indole-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
With hydrogen bromide In acetonitrile for 1h; Ambient temperature;

: 130288-24-3
(+)-duocarmycin SA

calf thymus DNA: calf thymus DNA

: (-)-duocarmycin SA-adenine adduct

Conditions

Conditions	Yield
With sodium phosphate buffer 1.) 25 deg C, 3 d, 2.) 100 deg C, 30 min; Yield given. Multistep reaction;

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