Retrosynthetically, 2 (Figure ) was envisioned to arise from a Cterminal Arg-Phe dipeptide unit and appendage of the two macrolactam subunits to the central valine residue, resulting in two fragments comprising a 17-membered (3, western fragment) and 12membered (4, eastern fragment) macrolactam, respectively. Our lab recently published a modular, atroposelective synthetic route to 1. While distinct in overall structure, the shared features of 1 and the western macrocycle of 2 suggested that the macrocyclization strategy employed in that synthesis may also be applicable herein to obtain 3. In order to generate the western fragment via Larock indole synthesis, the framework would be constructed from an asparagine unit, serine unit, alkyne fragment 5, and the requisite aniline in the form of a b-aryl asparagine. 4 was proposed to be constructed via macrocyclization along the His-Ser peptide bond. The overall synthetic strategy was centered around the construction of the bbranched amino acid units which are characteristic of the biosynthetic origin of 2 as a RiPP natural product. Key to the execution of this plan was that the branched AAs 6 and 8 could both be derived using the same nucleophilic ring-opening strategy upon aziridines 7 and 9, respectively (vide infra).