149405-54-9

Upstream product

• 128781-07-7 5,6,7-trimethoxy-1H-indole-2-carboxylic acid 
• 132628-69-4 methyl (2S*,8S*)-4-benzyloxy-1,2,3,6,7,8-hexahydro-8-hydroxymethyl-2-methyl-1-oxobenzo<1,2-b;4,3-b'>dipyrrole-2-carboxylate dihydrochloride 
• 132628-65-0 methyl 6-benzyloxy-1-t-butoxycarbonyl-3-(t-butyldimethylsilyloxy)methyl-2,3-dihydro-5-(1-methoxycarbonylethyl)amino-1H-indole-4-carboxylate 
• 149365-65-1 methyl 6-benzyloxy-1-t-butoxycarbonyl-3-(t-butyldimethylsilyloxy)methyl-2,3-dihydro-5-amino-1H-indole-4-carboxylate 
• 132628-67-2 methyl (2S*,8S*)-4-benzyloxy-6-t-butoxycarbonyl-8-(t-butyldimethylsilyloxy)methyl-3-formyl-1,2,3,6,7,8-hexahydro-2-methyl-1-oxobenzo<1,2-b;4,3-b'>dipyrrole-2-carboxylate 
• 132628-69-4 methyl (2R*,8S*)-4-benzyloxy-1,2,3,6,7,8-hexahydro-8-hydroxymethyl-2-methyl-1-oxobenzo<1,2-b;4,3-b'>dipyrrole-2-carboxylate dihydrochloride 
• 132628-67-2 methyl (2R*,8S*)-4-benzyloxy-6-t-butoxycarbonyl-8-(t-butyldimethylsilyloxy)methyl-3-formyl-1,2,3,6,7,8-hexahydro-2-methyl-1-oxobenzo<1,2-b;4,3-b'>dipyrrole-2-carboxylate 
• 157478-15-4 methyl (2S,8R)-4-benzyloxy-6-t-butoxycarbonyl-3-formyl-1,2,3,6,7,8-hexahydro-8-hydroxymethyl-2-methyl-1-oxobenzo<1,2-b;4,3-b'>dipyrrole-2-carboxylate 
• 149405-52-7 methyl (2S,8R)-8-<(S)-(1-acetoxy-1-phenyl)acetoxy>methyl-4-benzyloxy-6-t-butoxycarbonyl-3-formyl-1,2,3,6,7,8-hexahydro-2-methyl-1-oxobenzo<1,2-b;4,3-b'>dipyrrole-2-carboxylate 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 128781-06-6 methyl 2-azido-3-(3',4',5'-trimethoxyphenyl)-propenoate 
• 157485-07-9 methyl (Z)-2-azido-3-(3,4,5-trimethoxyphenyl)acrylate 
• 143874-45-7 3-acetoxymethyl-6-benzyloxy-2,3-dihydro-1H-indole 
• 143874-47-9 5-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxymethyl)-1,3-dioxo-3,4,8,9-tetrahydro-1H-[1,3]oxazino[5,4-e]indole-7-carboxylic acid tert-butyl ester 

Downstream Products

• 132628-71-8 methyl (2S*,8S*)-4-benzyloxy-1,2,3,6,7,8-hexahydro-8-(methanesulfonyloxy)methyl-2-methyl-1-oxo-6-<(5,6,7-trimethoxy-1H-indole-2-yl)carbonyl>benzo<1,2-b;4,3-b'>dipyrrole-2-carboxylate 
• 118292-34-5 dl-2-Epiduocarmycin A 
• 132628-71-8 methyl (2R*,8S*)-4-benzyloxy-1,2,3,6,7,8-hexahydro-8-(methanesulfonyloxy)methyl-2-methyl-1-oxo-6-<(5,6,7-trimethoxy-1H-indole-2-yl)carbonyl>benzo<1,2-b;4,3-b'>dipyrrole-2-carboxylate 
• 118292-34-5 dl-Duocarmycin A 
• 157478-21-2 methyl (2S,8R)-4-benzyloxy-1,2,3,6,7,8-hexahydro-8-(methanesulfonyloxy)methyl-2-methyl-1-oxo-6-<(5,6,7-trimethoxy-1H-indole-2-yl)carbonyl>benzo<1,2-b;4,3-b'>dipyrrole-2-carboxylate 

Relevant academic research and scientific papers

Synthetic Studies on Duocarmycin. 2. Synthesis and Cytotoxicity of Natural (+)-Duocarmycin A and Its Tree Possible Stereoisomers.

The title synthesis was achieved by featuring the optical resolution of two types of the tricyclic intermediates and the synthetic scheme established in the synthesis of racemic compounds.In vitro cytotoxicity assay against P388 murine leukemia obviously

Synthetic Studies on Duocarmycin. 1. Total Synthesis of dl-Duocarmycin A and Its 2-Epimer

The title synthesis was first achieved by employing novel methoxycarbonylation of the C4-position of the 5-aminoindoline by way of the isatin and subsequent Dieckmann cyclization to the methyl 2-methylindoxyl-2-carboxylate as key steps.In vitro cytotoxicity assay against P388 murine leukemia obviously disclosed that cytotoxicities of the synthesized compounds are comparable and almost half of that of natural (+)-duocarmycin A. - Key Words: dl-duocarmycin A, dl-2-epi-duocarmycin A, total synthesis, antitumor antibiotic, cytotoxicity

First total synthesis of dl-duocarmycin A

The title synthesis could be achieved by featuring introduction of a methoxycarbonyl group into the C-4 position of a 5-aminoindoline nucleus by way of an isatin derivative and subsequent ring closure to a methyl 2-methylindoxyl-2-carboxylate system by the Dieckmann cyclization.