Synthesis of the intermediate for fumimycin: a natural peptide deformylase inhibitor

Abstract

Synthetic efforts toward the potential bacterial peptide deformylase inhibitor fumimycin are reported. The synthetic approach features a tandem Friedel–Crafts alkylation/lactonization access as key reaction to the α, α-disubstituted amino acid unit, and results in the synthesis of an advanced racemic intermediate with an Z configuration propenyl group starting from vanillin with 18 % total yield in five steps.