The enantiospecific synthesis of (-)-monomorine from L-glutamic ester

Add time:09/26/2019    Source:sciencedirect.com

Diethyl L-glutamate hydrochloride (3) was converted to its N-pyrrole derivative 5. Submission of 5 to butyryl chloride in boiling toluene gave the 2-butyryl derivative, and by treatment with NaBH3CN and ZnI2, the 2-butyl analogue 9. Cyclization of 9 with BBr3 afforded (5S)-3-butyl-5-ethoxycarbonyl-5,6-dihydro-8(7H)-indolizinone (10). Hydrogenation of 10 over Pd/C in acidified EtOH gave (3S,5S,9R)-3-butyl-5-ethoxycarbonylindolizidine. By successive reduction of the latter to the primary alcohol, formation of the chloride and reductive dechlorination with tributyltin hydride, (3S,5R,9R)-3-butyl-5-methylindolizidine, or (-)-monomorine, was obtained in 8 steps from 3 in a yield of 25%.

We also recommend Trading Suppliers and Manufacturers of Diethyl L-glutamate hydrochloride (cas 1118-89-4). Pls Click Website Link as below: cas 1118-89-4 suppliers

Prev:Diethyl methyl chitosan as an intestinal paracellular enhancer: ex vivo and in vivo studies
Next:Research reportExcitatory amino acids in the forebrain of the Naples high-excitability rats: neurochemical and behavioural effects of subchronic d-aspartate and its diethyl ester prodrug)