Over the last twenty years, Mycobacterium tuberculosis has been the leading cause of death from any pathogen.[i] 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.[ii]^-,[iii],[iv] Herein, we describe the total synthesis of six congeners from the rufomycin family. Synthesis was achieved through the development of a divergent solid phase synthetic strategy, incorporating seven amino acids (four of which were accessed via novel syntheses) to provide linear peptide intermediates from a single resin-bound amino acid. These peptides were then subject to macrolactamization, protecting group removal, and late stage chemoselective oxidation to afford six natural products. Future work will include extensive screening of these natural products to investigate their anti-mycobacterial activity and potential as therapeutic leads to combat endemic TB infections.