Journal of Organic Chemistry p. 3223 - 3226 (1981)
Update date:2022-09-26
Topics:
Snider, Barry B.
Duncia, John V.
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.
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(1981)
