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The constrained aromatic α-amino acid 2 , 6 -dimethyl-β-methyl tyrosine (Figure 1) was designed to provide specific local constraints to peptides or peptide mimetics. We report here methods for the total asymmetric synthesis of all four stereoisomers. The precursors used were α,β-unsaturated acid derivatives, (2E) 3-(4 )-methoxy-2 ,6 -dimethyl-2-propenoic acid (5) and crotonyl chloride (6)...