79228-09-4

Upstream product

• 80249-82-7 C₁₈H₂₀N₂O₂ 
• 67045-81-2 [(2S,12bS)-3-Eth-(E)-ylidene-4-oxo-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl]-acetonitrile 
• 79235-44-2 (2S,12bS)-2-(4,4-Dimethyl-4,5-dihydro-oxazol-2-ylmethyl)-3-eth-(E)-ylidene-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizine 
• 79227-96-6 2-{[2-(1H-Indol-3-yl)-ethylcarbamoyl]-methyl}-malonic acid diethyl ester 
• 79228-02-7 (2R,12bS)-3-((R)-1-Methoxy-ethyl)-4-oxo-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizine-2-carboxylic acid ethyl ester 
• 79228-06-1 (2S,12bS)-2-(4,4-Dimethyl-4,5-dihydro-oxazol-2-ylmethyl)-3-eth-(E)-ylidene-2,3,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizin-4-one 
• 79228-03-8 (2R,3S,12bS)-2-Hydroxymethyl-3-((R)-1-methoxy-ethyl)-2,3,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizin-4-one 
• 79228-03-8 (2R,3R,12bS)-2-Hydroxymethyl-3-((R)-1-methoxy-ethyl)-2,3,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizin-4-one 
• 79233-46-8 [(2S,3R,12bS)-3-((R)-1-Methoxy-ethyl)-4-oxo-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl]-acetonitrile 
• 79233-46-8 [(2S,3S,12bS)-3-((R)-1-Methoxy-ethyl)-4-oxo-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl]-acetonitrile 
• 79227-99-9 2-[2-((2R,3R)-2-Bromo-3-methoxy-butyryl)-2,3,4,9-tetrahydro-1H-β-carbolin-1-ylmethyl]-malonic acid diethyl ester 
• 79228-01-6 (3R,12bR)-3-((S)-1-Methoxy-ethyl)-4-oxo-3,4,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizine-2,2-dicarboxylic acid diethyl ester 
• 79233-45-7 Methanesulfonic acid (2R,3R,12bS)-3-((R)-1-methoxy-ethyl)-4-oxo-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-ylmethyl ester 
• 79235-42-0 2-(2,3,4,9-Tetrahydro-1H-β-carbolin-1-ylmethyl)-malonic acid diethyl ester 

Relevant academic research and scientific papers

Chloroformate Ester-induced Reductive 1,2-Bond Cleavage of Some 1,2,3,4-Tetrahydro-β-carboline Derivatives

Treatment with a chloroformate ester at -70 deg C and subsequent reaction with NaBH3CN converts 1,2,5,6,11,11b-hexahydro-3H-indoloindolizine and derivatives of 1,2,3,4,6,7,12,12b-octahydroindoloquinolizine cleanly into the corresponding C/D

Chloroformate Ester-induced Reductive 1,2-Bond Cleavage of 1,2,3,4-Tetrahydro-β-carboline Derivatives: Stereochemistry and Application in Sequence with an Oxidative Bond Regeneration Reaction to the Synthesis of Indole Alkaloids

Treatment with a chloroformate ester at -70 deg C and subsequent reaction with NaBH3CN converts 1,2,5,6,11,11b-hexahydro-3H-indoloindolizine and derivatives of 1,2,3,4,6,7,12,12b-octahydroindoloquinolizine cleanly into corresponding C/D ring-cleaved urethane derivatives.Oxidation of the products with 1-chlorobenzotriazole in dichlormethane or in methanol as a participating solvent refunctionalises the centre, reduced during the cleavage reaction and permits a formal reversal of that reaction.The overall result in the case of the quinolizidine derivatives is partial epimerisation at C-12b, a process which is exemplified in the syntheses of methyl(+/-)-geissochizoate and akuammigine from their respective epimers.The sequence finds its application par excellence in the synthesis of the pentacyclic mavacurine skeleton, in wich chirality at C-12b is re-established dependently during ring regeneration after oxidation in the presence of Et3N.The same reaction provides test implications for an investigation of the stereochemistry of the reductive cleavage reaction, during wich the incorporation of deuterium (from NaBD3CN) is shown by chemical correlation to proceed with stereospecific inversion of configuration.

A NEW SYNTHESIS OF INDOLOQUINOLIZIDINE DERIVATIVES: A FORMAL TOTAL SYNTHESIS OF (+-)-GEISSOSCHIZINE

A stereospecific elimination process has been developed for introducing the E-ethylidene group in a transformation of tryptamine into methyl (+-)-geissoschizoate.