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