119184-21-3

Basic information

• Product Name: (1R,3S)-(+)-methyl 2,9-dibenzyl-3-(methoxycarbonyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate
• Synonyms: (1R,3S)-(+)-methyl 2,9-dibenzyl-3-(methoxycarbonyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate
• CAS NO: 119184-21-3
• Molecular Weight: 496.606
• Mol File: 119184-21-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (1R,3S)-(+)-methyl 2,9-dibenzyl-3-(methoxycarbonyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,3S)-(+)-methyl 2,9-dibenzyl-3-(methoxycarbonyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate(119184-21-3)
• EPA Substance Registry System: (1R,3S)-(+)-methyl 2,9-dibenzyl-3-(methoxycarbonyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate(119184-21-3)

Safety Data

• Hazardous Substances Data: 119184-21-3(Hazardous Substances Data)

Upstream product

• 142230-29-3 (+)-cis-methyl 2,9-dibenzyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate 
• 67-56-1 methanol 
• 129708-74-3 (3S)-(+)-2,9-dibenzyl-3-(methoxycarbonyl)-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionic acid 
• 186581-53-3 diazomethane 
• 328-50-7 α-ketoglutaric acid 
• 119184-20-2 (S)-(-)-N,N'-dibenzyltryptophan methyl ester 
• 100-52-7 benzaldehyde 
• 129784-64-1 N¹-benzyl-(L)-tryptophan methyl ester 
• 129708-73-2 (S)-3-(1-Benzyl-1H-indol-3-yl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid methyl ester 

Downstream Products

• 119184-23-5 (6R,10R)-(+)-methyl 5,12-dibenzyl-9-oxo-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole-8-carboxylate 
• 119184-23-5 C₃₀H₂₈N₂O₃ 
• 119184-25-7 C₂₁H₂₀N₂O 
• 119184-26-8 C₂₄H₂₂N₂O 
• 119184-24-6 C₂₃H₂₂N₂O₃ 
• 119184-30-4 [(2S,6R,12bR)-12-Benzyl-13-methylene-1,7,12,12b-tetrahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizin-(3E)-ylidene]-acetic acid methyl ester 
• 119184-33-7 2-[(2R,6R,12bR)-12-Benzyl-13-hydroxymethyl-1,7,12,12b-tetrahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizin-(3E)-ylidene]-ethanol 
• 119184-31-5 C₂₈H₂₈N₂O₂ 
• 119184-28-0 C₂₆H₂₄N₂O₃ 
• 119184-32-6 [(2R,6R,12bR)-12-Benzyl-13-hydroxymethyl-1,7,12,12b-tetrahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizin-(3E)-ylidene]-acetic acid methyl ester 
• 119184-27-9 C₃₂H₃₈N₂O₃Si 
• 19452-84-7 (+)-taberpsychine 
• 604-99-9 E-koumidine 
• 119184-29-1 [(2S,6R,12bR)-12-Benzyl-13-oxo-1,7,12,12b-tetrahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizin-(3Z)-ylidene]-acetic acid methyl ester 

Relevant articles and documents

STEREOSPECIFICITY IN THE PICTET-SPENGLER REACTION. ENANTIOSPECIFIC SYNTHESIS OF (6S,10S)-(-)-5-METHYL-9-OXO-12-BENZYL-6,7,8,9,10,11-HEXAHYDRO-6,10-IMINO-5H-CYCLOOCTINDOLE, A TEMPLATE FOR PREPARATION OF MACROLINE/SARPAGINE ALKALOIDS

The synthesis of the tetracyclic ketone was carried out in enantiospecific fashion (>98percent ee) via the 1,3-transfer of chirality from Na-methyl, Nb-benzyl tryptophan methyl ester to the trans diastereomer in the Pictet-Spengler reaction.Although the condensation of 14 with aldehyde (15) in refluxing benzene generated the tetrahydro β-carbolines (4b/5b) in a kinetic ratio (72:28), epimerization (C-1) of the cis diastereomer into the trans isomer occurred stereospecifically under acidic conditions.Dieckmann cyclizatin of either the Na-methyl, Nb-benzyl-cis-(+)-5b or trans-(-)-4b diastereomer provided the cis-bicyclo-azanonane system at approximately the same rate, although the β-keto esters were antipodal, in contrast to results reported in the Na-benzyl series by Magnus.

Total synthesis of (+)-koumine, (+)-taberpsychine, and (+)-koumidine

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