Synthesis of methyl-3-orsellinate by organic synthesis or by altered biosynthetic pathways using lichen immobilisates

Abstract

Methyl-3-orsellinate can be generated from methyl-3-orcinol through the nitration of aryl function to be then reduced to amine group. This last derivative could be the substrat of a diazotonization for the corresponding diazonium salt. After this, a cyanide group could be introduced by nucleophilic substitution using potassium cyanide and then, the carboxyl function could be produced after hydrolysis. Alternatively, methyl-3-orsellinate could be produced by alginate-immobilized, atranorin-producing lichen cells loaded with acetate and treated with sodium azide. Acetate is used by acetyl-CoA carboxylase and aromatic synthase (methyl transfer) to produce methyl-3-orsellinate and its oxidation to haematommoyl alcohol is inhibited by sodium azide.