Modular Total Synthesis of Farnesyl Analogues of Cell Wall Precursors Lipid I and II Containing the Staphylococcus aureus Pentaglycine Bridge Modification

A scalable and modular total synthesis of 3-lipid I and 3-lipid II was accomplished by a novel route involving an efficient solid phase synthesis of the peptide fragment and an effective chemoenzymatic attachment of the second sugar moiety. The generality of this route was further documented by the synthesis of an analogue bearing the pentaglycine interpeptidic bridge modification characteristic for the human pathogen Staphylococcus aureus.