Towards the total synthesis of ellagic acid analogues – regioselective functionalisation of gallic acid’s phenolic functions

Malaria remains a worldwide major health issue. Therefore, there is an urgent need in new antiplasmodials. In this context, ellagic acid appears to be a good starting point. Recent researches have led to the synthesis of gallic acid linear dimers. This work aims to regioselectively modulate the phenolic functions of the gallic acid which is the monomer used in the total synthesis of ellagic acid. Different organic groups such as methyl, ethyl, fluoroethyl, hydroxyethyl and aminoethyl are grafted on the phenolic functions and lead to the formation of several compounds with various size and polarity. This work showed that while alkylation of phenol at the meta-position of the carboxylic acid is achieved in good yields, the alkylation of phenol at the para-position needs further optimization. The synthetized compounds were analysed by NMR, mass spectrometry, elementary analysis and their melting point were determined. In addition to the total synthesis of ellagic acid analogues, this work also allows the gallic acid’s pharmacomodulation. The monomers which have been synthetized will soon be tested to determine their antimalarial activity.