RACEMIC SYNTHESIS OF METHOXYLATED CARAMBOXIN
Brazilian researchers isolated in 2013 the compound responsible for the possible neurotoxic effects caused by the ingestion of star fruit (Averrhoa carambola) - caramboxin. The neurotoxin structure contains a phenylalanine backbone and the absolute configuration of the α-amino acid carbon was only inferred by comparing the signal of the L-phenylalanine [α] D values and the compound in question. Chirality is closely related to the biological activity of the molecule, and therefore for further proof of its absolute configuration this project will focus on synthetic studies of this compound in racemic form. The proposed route for caramboxin synthesis involves 3,5-dimethoxybenzoic acid as a starting material, following another reaction of the product of this reaction undergoes insertion of the formyl group (-CHO) and consequent oxidation via Lindgren reaction as a key step of the synthetic route. If the results are satisfactory and the reaction yields, in the end the product obtained will hydrolyze to the methoxylated caramboxin and in racemic form.