128781-06-6

Upstream product

• 1816-92-8 Methyl azidoacetate 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 637-81-0 ethyl-2-azidoacetate 
• 124-41-4 sodium methylate 

Downstream Products

• 118292-34-5 dl-Duocarmycin A 
• 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 
• 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 
• 132628-70-7 methyl (2R*,8S*)-4-benzyloxy-1,2,3,6,7,8-hexahydro-8-hydroxymethyl-2-methyl-1-oxo-6-<(5,6,7-trimethoxy-1H-indole-2-yl)carbonyl>benzo<1,2-b;4,3-b'>dipyrrole-2-carboxylate 
• 132628-70-7 methyl (2S*,8S*)-4-benzyloxy-1,2,3,6,7,8-hexahydro-8-hydroxymethyl-2-methyl-1-oxo-6-<(5,6,7-trimethoxy-1H-indole-2-yl)carbonyl>benzo<1,2-b;4,3-b'>dipyrrole-2-carboxylate 
• 128781-07-7 5,6,7-trimethoxy-1H-indole-2-carboxylic acid 
• 853134-00-6 methyl 3-formyl-5,6,7-trimethoxy-N-methylindole-2-carboxylate 
• 118292-37-8 5,6,7-trimethoxy-1H-indole-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Regioselective reactivity of some 5,7-dimethoxyindoles

The reactivity of some 5,7-dimethoxyindoles with respect to electrophiles has been investigated. The favoured sites for reaction are C3 and C4 and regioselectivity can be controlled by the judicious arrangement of electron-withdrawing substituents. Results of formylation, acylation, the Mannich reaction, bromination and nitration are described.

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.