197657-11-7

Upstream product

• 204779-24-8 (3S)-3-acetoxymethyl-5-[1-(methoxycarbonyl)ethyl]amino-6-benzyloxy-1-t-butoxycarbonylindoline 
• 62-23-7 4-nitro-benzoic acid 
• 600-22-6 pyruvic acid methyl ester 

Downstream Products

• 197657-12-8 methyl (1S)-5-benzyloxy-3-t-butoxycarbonyl-1-hydroxymethyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-7-carboxylate 
• 197657-13-9 methyl (1S)-5-benzyloxy-3-t-butoxycarbonyl-1-chloromethyl-1,2,3,6-tetrahydropyrrolo[3,2-e]indole-7-carboxylate 
• 144667-38-9 duocarmycin 
• 130288-24-3 (+)-duocarmycin SA 

Relevant academic research and scientific papers

Intermediates for the preparation of duocarmycin SA and derivatives thereof, and process for the production of the intermediates

PCT No. PCT/JP97/02207 Sec. 371 Date Mar. 9, 1999 Sec. 102(e) Date Mar. 9, 1999 PCT Filed Jun. 26, 1997 PCT Pub. No. WO98/12197 PCT Pub. Date Mar. 26, 1998Indole derivatives shown by the formulae (1), (2a) and (2b) (wherein R1 is a protecting group for am

A novel synthesis of (+)-duocarmycin SA

The title synthesis was achieved in eight steps from (S)-5-aminoindoline (S)-4 by a method featuring sequential dehydrogenation, double bond isomerization, and oxidative cyclization of (S)-5-[(1-methoxycarbonylethyl)amino]indoline 5 as the key steps. The sequential reaction was effected by using MnO2-Pd(OAc)2 as the oxidizing agent in the presence of an acid catalyst.