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. Author manuscript; available in PMC: 2012 Jul 28.
Published in final edited form as: J Med Chem. 2011 Jun 28;54(14):4954–4963. doi: 10.1021/jm1016126

Scheme 1.

Scheme 1

Retrosynthesis of arylomycin C16. Arylomycin derivatives were synthesized by modification of previously reported protocols.20,34 Briefly, tripeptide macrocycle precursor was synthesized by solution phase peptide couplings and then cyclized via Suzuki-Miyaura macrocyclization. The various lipopeptide tails were assembled via solution phase peptide couplings and then coupled to the macrocyclic core, or the glycine-homologated macrocycle core.