174868-46-3

Upstream product

• 64-19-7 acetic acid 
• 174868-57-6 (R)-4-Benzyloxy-8-hydroxy-8,9-dihydro-3H,7H-pyrrolo[3,2-f]quinoline-2,6-dicarboxylic acid dimethyl ester 
• 62-23-7 4-nitro-benzoic acid 
• 757951-83-0 methyl 7-benzyloxy-1-methanesulfonyl-5-(N-methoxycarbonylamino)-4-(1-propyn-3-ol)indole-2-carboxylate 
• 757951-84-1 7-benzyloxy-4-(3-hydroxy-propenyl)-1-methanesulfonyl-5-methoxycarbonylamino-1H-indole-2-carboxylic acid methyl ester 
• 757951-82-9 methyl 7-benzyloxy-4-iodo-1-methanesulfonyl-5-(N-methoxycarbonylamino)indole-2-carboxylate 
• 121-88-0 5-Nitro-2-aminophenol 
• 757951-81-8 5-amino-7-benzyloxy-4-iodo-1-methanesulfonyl-1H-indole-2-carboxylic acid methyl ester 
• 757951-76-1 methyl 7-benzyloxy-1-methanesulfonyl-5-nitroindole-2-carboxylate 
• 757951-79-4 C₁₅H₁₅IN₂O₇S₂ 
• 757951-80-7 5-amino-7-benzyloxy-1-methanesulfonyl-1H-indole-2-carboxylic acid methyl ester 
• 757951-77-2 N-methanesulfonyl-2-benzyloxy-6-iodo-4-nitroaniline 
• 757951-78-3 2-iodo-4-nitro-6-(phenylmethoxy)benzenamine 
• 100-39-0 benzyl bromide 

Downstream Products

• 757951-86-3 methyl 4-(benzyloxy)-3,7,8,9-tetrahydro-8-methanesulfonyloxy-6-(methoxycarbonyl)-6H-pyrrolo[3,2-f]quinoline-2-carboxylate 
• 174868-40-7 methyl 4-(benzyloxy)-3,7,8,9-tetrahydro-8-hydroxy-6-(methoxycarbonyl)-6H-pyrrolo[3,2-f]quinoline-2-carboxylate 

Relevant academic research and scientific papers

New synthetic method for indole-2-carboxylate and its application to the total synthesis of duocarmycin SA

(Equation Presented) The sequential coupling and cyclization reactions between aryl halides and methyl propiolate were investigated. The electron-withdrawing groups on the aromatic ring are essential for producing the methyl indole-2-carboxylate derivativ

Preparation of alkyl-substituted indoles in the benzene portion. Part 14. Synthesis of (±)-duocarmycin SA, natural (+)-duocarmycin SA and non-natural (-)-duocarmycin SA

Total synthesis of duocarmycin SA (1), an extremely potent cytotoxic antibiotic, was achieved in the racemic form at first by effectively utilizing two reactions as key steps, (i) an intramolecular Heck reaction of the benzyl ether 21a, derived from a dihydropyridine 13a and a pyrrole derivative 11, to form tricyclic compounds 25a and 26a, and (ii) a modified Mitsunobu reaction on the diol derivative 40 for the construction of compound 41 having the pivotal pharmacophore of a cyclopropanoindolinone partial structure, which is critical for the high biological activities of 1. Next, optical resolution of an intermediary racemic secondary alcohol 50 was cleanly attained by derivatizing it to (R)-O-methylmandelates 52 and 53, and the resulting chiral alcohols (+)-50 and (-)-50 were respectively transformed into unnatural (-)-1 and natural (+)-1. Finally inversion of the secondary alcohol (+)-50 to the enantiomer (-)-50 was effected by using the Mitsunobu reaction. This constitutes an enantio-convergent total synthesis of natural duocarmycin SA (1) starting from a racemic compound.