Synthetic analogues of the antibiotic pestalone

The first synthetic study towards the natural product pestalone () is described culminating in the preparation of selected n−1 analogues. Pestalone is a chlorinated and prenylated benzophenone antibiotic, which is of interest due to a strong activity against methicillin-resistant staphylococcus aureus strains (MRSA). Key step of the synthesis is the nucleophilic addition of a highly functionalized aryllithium building block to a 2-prenylated 3,5-dialkoxy-benzaldehyde followed by oxidation. For the introduction of the prenyl sidechain by aryl-allyl coupling, different procedures were evaluated, among them the Stille reaction and a nickel π-allyl complex coupling.