T. Kwon, P. F. Keusenkothen, Michael B. Smith
Nov 1, 1992
Citations
0
Influential Citations
34
Citations
Journal
Journal of Organic Chemistry
Abstract
The potent inhibitor of 4-aminobutyrate-2-oxoglutarate aminotransferase (GABA-T), 4-aminohex-5-enoic acid (vinyl GABA), has been synthesized with excellent enantioselectivity in six steps from L-glutamic acid in an overall yield of 33%. This is the most efficient synthesis of this important compound and illustrates the use of a novel alkenyl protecting group for pyroglutamate. This allowed the preparation and manipulation of the key (S)-2-oxopyrrolidine-5-carboxaldehyde intermediate