In this report, we compared macrocycles with changes to the backbone aromatic group, but no changes to the peptides amino acids to be able to compare subtle differences. All compounds were designed based on the natural product Sanguinamide A and synthesized based on a previously reported total synthesis, which required the preparation of a dipeptide building block with the pyridine fragment. Oxidation of the pyridine nitrogen was necessary to increase the nucleophilicity of the amine in the 2 position. The obtained intermediates gave us the opportunity to test the pyridine N-oxide macrocycles as well. For all benzene analogues, a dipeptide was not required, and they were directly incorporated during SPPS as Fmocprotected building blocks.