Improved Synthesis of the Biologically Active Methionine Analog, L-2-Amino-4-methoxy-cis-but-3-enoic Acid (L-cis-amb) Using an Electrophilic Glycinate Synthon

Abstract

An improved synthesis of the methionine analog L-cis-AMB, is reported. The key step involves condensation of cis-methoxyvinyllithium with N-acetyl-α-bromoglycine methyl ester to give N-acetyl-DL-cis-AMB methyl ester, the penultimate intermediate of L-cis-AMB synthesis.