916667-93-1

Upstream product

• 1033193-65-5 (1S,10R)-5-benzyloxy-3-(tert-butoxycarbonyl)-1-(10-hydroxyethyl)-1,2-dihydro-3H-benz[e]indole 

Downstream Products

• 945674-96-4 (+)-{(1S,10R)-5-benzyloxy-1-(10-chloroethyl)-3-[(5-(1-methylpiperidin-4-yl-methoxy)-indol-2-yl)-carbonyl]-1,2-dihydro-3H-benz[e]indole} 
• 945674-95-3 (+)-{(1S,10R)-5-benzyloxy-1-(10-chloroethyl)-3-[(5-(2-morpholin-4-yl-ethoxy)-indol-2-yl)-carbonyl]-1,2-dihydro-3H-benz[e]indole} 
• 945674-94-2 (+)-{(1S,10R)-5-benzyloxy-1-(10-chloroethyl)-3-[(5-(2-N,N-dimethylaminoacetylamino)-indol-2-yl)-carbonyl]-1,2-dihydro-3H-benz[e]indole} 
• 945674-93-1 (+)-{(1S,10R)-5-benzyloxy-1-(10-chloroethyl)-3-[(5-(2-N,N-dimethylaminoethoxy)-6-methoxy-indol-2-yl)-carbonyl]-1,2-dihydro-3H-benz[e]indole} 
• 945674-83-9 (+)-{(1S,10R)-5-benzyloxy-1-(10-chloroethyl)-3-[(5-(2-N,N-dimethylaminoethoxy)-indol-2-yl)-carbonyl]-1,2-dihydro-3H-benz[e]indole} 

Relevant academic research and scientific papers

Enantio- And diastereoselective synthesis of duocarmycine-based prodrugs for a selective treatment of cancer by epoxide opening

For the enantio- und diastereoselective synthesis of the prodrug 2, the N-tert-butyloxycarbonyl-protected amine 7 was alkylated with the enantiopure epoxide 14 to give the amide 10. A regio- and facial-selective metal-mediated cyclisation by using a cuprate led to 17 with an inversion of configuration at C10. Subsequent transformation of the hydroxy group in 17 by using the Appel procedure afforded (1S, 10R)-9 with an unusual double inversion owing to neighbouring-group participation of the N-tert-butoxycarbonyl group. (1S, 10R)-9 is the key intermediate in the synthesis of the prodrug 2, which has been developed for a selective treatment of cancer based on the antibody-directed enzyme prodrug therapy as an analogue of the natural antibiotic duocarmycine SA (1).