8th Annual WML Academic Symposium

Presenter(s): Benjamin Abraham
Title: Synthesis of Levodopa from Tyrosine via Aromatic Substitution Reactions
Developed under the guidance of Dr. Elizabeth Blue , Chemistry

Levodopa (3,4-dihydroxyphenylalanine) is a compound used to treat Parkinson’s Disease. Commercial syntheses include tyrosine hydroxylase- catalyzed aromatic hydroxylation from tyrosine and five-step synthesis from vanillin. The project goal is safe, inexpensive, and effective synthesis of levodopa from tyrosine for future organic teaching laboratory use. The initial synthesis plan was copper(I)-catalyzed hydroxylation of a substituted tyrosine. Substitutions trialed included halogenation with hypochlorite, chlorate, or oxone and sulfonation. Iron(II)-catalyzed direct hydroxylation with hydrogen peroxide is being investigated to potentially reduce the reaction to one step. The results of the experiments investigating these synthetic routes are to be discussed in this presentation.