55950-18-0

Upstream product

• 100-39-0 benzyl bromide 
• 55950-19-1 2-Aza-7-exo-methylbicyclo<4.4.0>deca-3-one 
• 188350-98-3 1-benzyl-5-methyl-3,4,5,6,7,8-hexahydro-1H-quinolin-2-one 
• 188350-97-2 1-benzyl-5-methyl-5,6,7,8-tetrahydro-1H-quinolin-2-one 
• 188350-96-1 1-benzyl-3-(ethylsulfenyl)-5-methyl-5,6,7,8-tetrahydro-1H-quinolin-2-one 
• 188350-88-1 N-benzyl(ethylsulfinyl)-N-(5-methylhept-6-enoyl)acetamide 
• 269405-68-7 trifluoromethanesulfonic acid 1-benzyl-5-methyl-2-oxo-1,2,5,6,7,8-hexahydroquinolin-3-yl ester 

Downstream Products

• 86197-24-2 (4aα,5α,8aα)-1-benzyl-5-methyl-3,4,4a,5,6,7,8,8a-octahydroquinolinium perchlorate 
• 86197-08-2 (2S,4aS,5R,8aR)-1-Benzyl-5-methyl-2-pent-1-ynyl-decahydro-quinoline 

Relevant academic research and scientific papers

The tandem Pummerer-isomunchnone route to (±)-pumiliotoxin C

The Pummerer reaction of imidosulfoxides containing tethered π-bonds results in the formation of isomunchnone dipoles which readily undergo intramolecular dipolar cycloaddition to furnish 5-substituted α-pyridones. An application of the method to (±)-pumiliotoxin C was carried out.

Importance of allylic interactions and stereoelectronic effects in dictating the steric course of the reaction of iminium ions with nucleophiles. An efficient total synthesis of (±) gephyrotoxin

A stereocontrolled total synthesis of (±)-gephyrotoxin in 15 steps and 6.5% overall yield from benzyl trans-1,3-butadiene-1-carbamate is described. A key step is reduction of octahydroquinoline 27 from the more hindered concave α face to provide decahydroquinoline 28. This unusual transformation results from the interplay of allylic (A1,2) steric interactions and stereoelectronic effects.