Stereospecific Syntheses of Both Diastereomers of (+/-)-2-Amino-4-methyl-5-hexenoic Acid.

Article abstract of DOI:10.1021/jo00329a015

Both diastereomers of 2-amino-4-methyl-5-hexenoic acid (7 and 16) have been synthesized stereospecifically from methyl (2R^*,4S^*)-2-bromo-4-methyl-5-hexenoate (1), the product of the EtAlCl2-catalyzed ene reaction of methyl α-bromoacrylate and trans-2-butene.This synthesis establishes the stereochemistry of the ene reaction and establishes that the amino isolated from a Streptomyces fermentation is 7.