79328-88-4

Basic information

• Product Name: methyl 2-(benzyloxycarbonyl)-7-exo-(1-phenylsulfonylindol-2-yl)-2-azabicyclo[2.2.2]oct-5-ene-7-endo-carboxylate
• Synonyms: methyl 2-(benzyloxycarbonyl)-7-exo-(1-phenylsulfonylindol-2-yl)-2-azabicyclo[2.2.2]oct-5-ene-7-endo-carboxylate
• CAS NO: 79328-88-4
• Molecular Weight: 556.639
• Mol File: 79328-88-4.mol

Chemical Properties

• CAS DataBase Reference: methyl 2-(benzyloxycarbonyl)-7-exo-(1-phenylsulfonylindol-2-yl)-2-azabicyclo[2.2.2]oct-5-ene-7-endo-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-(benzyloxycarbonyl)-7-exo-(1-phenylsulfonylindol-2-yl)-2-azabicyclo[2.2.2]oct-5-ene-7-endo-carboxylate(79328-88-4)
• EPA Substance Registry System: methyl 2-(benzyloxycarbonyl)-7-exo-(1-phenylsulfonylindol-2-yl)-2-azabicyclo[2.2.2]oct-5-ene-7-endo-carboxylate(79328-88-4)

Safety Data

• Hazardous Substances Data: 79328-88-4(Hazardous Substances Data)

Upstream product

• 79328-85-1 N-benzyloxycarbonyl-1,2-dihydropyridine 
• 74185-41-4 methyl α-methylene-1-(phenylsulfonyl)-1H-indole-2-acetate 
• 501-53-1 benzyl chloroformate 
• 110-86-1 pyridine 

Downstream Products

• 79328-94-2 (1R,4R,6R)-6-(1H-Indol-2-yl)-2-aza-bicyclo[2.2.2]oct-7-ene-2,6-dicarboxylic acid 2-benzyl ester 6-methyl ester 
• 133372-41-5 Methyl 2-(Benzyloxycarbonyl)-7,8-exo,exo-dihydroxy-6-exo-<1-(phenylsulfonyl)indol-2-yl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate 
• 79329-02-5 (1R,4S,6R)-6-(1-Benzenesulfonyl-1H-indol-2-yl)-2-aza-bicyclo[2.2.2]octane-6-carboxylic acid methyl ester 
• 79328-95-3 methyl 7-exo-(1-phenylsulfonylindol-2-yl)-2-azabicyclo[2.2.2]oct-5-ene-7-endo-carboxylate 
• 133372-42-6 Isopropylidene Derivative of Methyl 2-(Benzyloxycarbonyl)-7,8-exo,exo-dihydroxy-6-exo-<1-(phenylsulfonyl)indol-2-yl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate 
• 133399-33-4 Isopropylidene Derivative of Methyl 7,8-exo,exo-Dihydroxy-6-exo-(3-iodoindol-2-yl)-2-<2-(phenylsulfonyl)prop-2-enyl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate 
• 133372-46-0 20-Deethyl-15,20-exo,exo-dihydroxy-5a-(phenylsulfonyl)-5,6-homocoronaridine 
• 133372-43-7 Isopropylidene Derivative of Methyl 7,8-exo,exo-Dihydroxy-6-exo-<1-(phenylsulfonyl)indol-2-yl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate 
• 133372-45-9 Isopropylidene Derivative of Methyl 7,8-exo,exo-Dihydroxy-6-exo-indol-2-yl-2-<2-(phenylsulfonyl)prop-2-enyl>-2-azabicyclo<2.2.2>octane-6-endo-carboxylate 
• 79328-99-7 1-benzenesulfonyl-6-nor-15-methoxy-15,20-dihydro-20-deethylcatharantine 
• 79329-05-8 C₂₅H₂₆N₂O₄S 
• 79329-03-6 C₂₄H₂₄N₂O₄S 
• 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 
• 79328-96-4 1-benzenesulfonyl-6-nor-20-deethylcatharanthine 

Relevant articles and documents

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.