79328-95-3

Upstream product

• 79328-85-1 N-benzyloxycarbonyl-1,2-dihydropyridine 
• 110-86-1 pyridine 
• 79328-86-2 1-(phenoxycarbonyl)-1,2-dihydropyridine 
• 74185-41-4 methyl α-methylene-1-(phenylsulfonyl)-1H-indole-2-acetate 
• 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 
• 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

• 79328-99-7 1-benzenesulfonyl-6-nor-15-methoxy-15,20-dihydro-20-deethylcatharantine 
• 74195-04-3 (1S,4S,6S)-6-(1-Benzenesulfonyl-1H-indol-2-yl)-2-aza-bicyclo[2.2.2]oct-7-ene-2,6-dicarboxylic acid dimethyl ester 
• 79329-05-8 C₂₅H₂₆N₂O₄S 

Relevant academic research and scientific papers

Synthesis and oxidative fragmentation of catharanthine analogs. Comparison to the fragmentation - Coupling of catharanthine and vindoline

Two new analogs of catharanthine have been synthesized in racemic form. They differ from catharanthine in the fusion of the indole ring to the non- aromatic portion of the iboga skeleton, with the [2,3] fusion present in catharanthine being replaced by [2,1] and [3,2] fusions. The corresponding deethyl analogs were also and methodological improvements were applied to an existing synthesis of deethylcatharanthine and a formal synthesis of racemic catharanthine. The reactivity of the catharanthine analogs toward coupling with vindoline was examined. Coupling was attempted by both the amine oxide fragmentation (Potier) and Fe3+ methods. Under Potier conditions the [2,1] fused analogs give low yields of coupling products in which vindaline is attached to the 3-position of the indole ring. The [3,2] isomers undergo fragmentation of the C16-C21 bond, as observed for catharanthine, but no coupling to vindoline occurs. The reactivity, oxidation potentials and conformation of the analogs are compared with catharanthine, deethylcatharanthine and N-methylcatharanthine.

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.