Mycobacterium tuberculosis is currently the leading cause of death from an infectious agent.1 With growing drug resistance amongst strains of these mycobacteria, research into novel, potent antibacterial agents is needed to combat this urgent health crisis. Rufomycins are a class of cyclic non-ribosomal heptapeptides produced by the deep sea-dwelling Streptomyces atratus that exhibit potent antimycobacterial activity.2,3 Herein we describe the total synthesis of eight different congeners within the rufomycin family, including both prenylated and epoxide-bearing members, as well several bicyclic congeners. Synthesis was achieved through the development of a divergent solid phase synthetic strategy, incorporating amino acids (six of which were accessed via novel syntheses) to provide linear peptide intermediates from a single loaded amino acid. These peptides were then subjected to macrolactamization, late stage chemoselective oxidation, and secondary cyclisation to afford the natural products.