Mycobacterium tuberculosis (TB) produces mycobactins, a family of non-ribosomally produced peptidic sideropores that scavenge iron from the iron-poor interior of macrophages where TB grows. Recently, dideoxy analogs of mycobactins, in which the hydroxyamides are reduced to amides, have been identified as antigens that bind to CD1a, a nonpolymorphic analog of MHC class I antigen presenting molecules. To facilitate ongoing studies of DDM in clinical studies and more detailed studies of the structural specificity of the CD1a-DDM-T cell receptor complex, we designed a convenient method for chemical synthesis using Fmoc-based solid phase peptide synthesis (SPSS) chemistry. In addition to conventional peptide linkages, DDM also includes an ester linkage, a salicylic acid-based oxazoline ring structure, a cyclized N-terminal lysine, and an acyl group which require modifications of commonly used peptide synthesis techniques. Solid phase peptide synthesis techniques are presented for the successful preparation of antigenic DDM. Solvent choices are of particular importance. The developed methodology enabled the facile synthesis of antigenic DDM.