Catalytic asymmetric synthesis of the common amino acid component in the biosynthesis of tetrahydroisoquinoline alkaloids

Abstract

Biosynthetic assembly lines of tetrahydroisoquinoline alkaloids employ the tyrosine derivative, (S)-2-amino-3-(3-hydroxy-4-methoxy-5-methylphenyl)propanoic acid, as a common amino acid building block. A catalytic asymmetric synthetic route to the common amino acid component has been developed by making use of Maruoka’s chiral phase transfer alkylation of a glycine derivative with the requisite benzyl bromide.