79328-94-2

Upstream product

• 110-86-1 pyridine 
• 501-53-1 benzyl chloroformate 
• 79328-85-1 N-benzyloxycarbonyl-1,2-dihydropyridine 
• 79328-88-4 methyl 2-(benzyloxycarbonyl)-7-exo-(1-phenylsulfonylindol-2-yl)-2-azabicyclo[2.2.2]oct-5-ene-7-endo-carboxylate 

Downstream Products

• 133372-62-0 (1S,4S,6S)-6-(3-Iodo-1H-indol-2-yl)-2-aza-bicyclo[2.2.2]oct-7-ene-2,6-dicarboxylic acid 2-benzyl ester 6-methyl ester 
• 133372-65-3 (1S,4S,6S)-6-[3-((E)-2-Methoxycarbonyl-vinyl)-1-methyl-1H-indol-2-yl]-2-aza-bicyclo[2.2.2]oct-7-ene-2,6-dicarboxylic acid 2-benzyl ester 6-methyl ester 
• 133372-64-2 (1S,4S,6S)-6-[3-((E)-2-Methoxycarbonyl-vinyl)-1H-indol-2-yl]-2-aza-bicyclo[2.2.2]oct-7-ene-2,6-dicarboxylic acid 2-benzyl ester 6-methyl ester 
• 133372-63-1 (1S,4S,6S)-6-(3-Iodo-1-methyl-1H-indol-2-yl)-2-aza-bicyclo[2.2.2]oct-7-ene-2,6-dicarboxylic acid 2-benzyl ester 6-methyl ester 

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.