74195-04-3

Upstream product

• 110-86-1 pyridine 
• 120-72-9 indole 
• 40899-71-6 1-benzenesulfonylindole 
• 98-09-9 benzenesulfonyl chloride 
• 74185-40-3 Methyl 2-(1-benzenesulfonylindol-2-yl)-2-hydroxypropionate 
• 79328-87-3 (1S,4S,6S)-6-(1-Benzenesulfonyl-1H-indol-2-yl)-2-aza-bicyclo[2.2.2]oct-7-ene-2,6-dicarboxylic acid 2-tert-butyl ester 6-methyl ester 
• 66531-21-3 1-<(2,2,2-trichloroethoxy)carbonyl>-1,2-dihydropyridine 
• 79-22-1 methyl chloroformate 
• 79328-95-3 methyl 7-exo-(1-phenylsulfonylindol-2-yl)-2-azabicyclo[2.2.2]oct-5-ene-7-endo-carboxylate 
• 79328-90-8 (1S,4S,6S)-6-(1-Benzenesulfonyl-1H-indol-2-yl)-2-aza-bicyclo[2.2.2]oct-7-ene-2,6-dicarboxylic acid 6-methyl ester 2-(2,2,2-trichloro-ethyl) ester 
• 33707-36-7 1-(methoxycarbonyl)-1,2-dihydropyridine 
• 74185-41-4 methyl α-methylene-1-(phenylsulfonyl)-1H-indole-2-acetate 
• 79328-88-4 methyl 2-(benzyloxycarbonyl)-7-exo-(1-phenylsulfonylindol-2-yl)-2-azabicyclo[2.2.2]oct-5-ene-7-endo-carboxylate 
• 79328-86-2 1-(phenoxycarbonyl)-1,2-dihydropyridine 

Relevant academic research and scientific papers

Diels-Alder Adducts of 1-Benzenesulfonylindole-2-acrylates and 1-(Alkoxycarbonyl)-1,2-dihydropyridines. Intermediates for Synthesis of Iboga Alkaloid Analogues

Diels-Alder reactions between methyl 1-benzenesulfonylindole-2-acrylate and several 1-(alkoxycarbonyl)-1,2-dihydropyridines give protected methyl 7-(2-indolyl)-2-azabicyclooctene-7-carboxylates which serve as intermediates for the synthesis of analogues of the iboga alkaloids.Methods for deprotection of both the carbamate nitrogen and indole nitrogen are reported.The 7-(2-indolyl)-2-azabicyclooctene-7-carboxylates show a tendency to undergo fragmentation of the C-1,C-7 bond of the 2-azabicyclooctene ring, probably by retro-Mannich reactions.Several 6-nor-20-deethyl analogues of catharanthine have been prepared from intermediates derived from the deprotected Diels-Alder adducts.

Chloroacetamide Photocyclization. Synthesis of 20-Deethylcatharanthine

20-Deethylcatharanthine, a potential precursor of vinblastine-type dimeric indole alkaloids, has been synthesized in ten steps from 1-benzenesulfonylindole.The Synthesis features a Diels-Alder reaction between 1-carbethoxy-1,2-dihydropyridine and ethyl 2-