In addition to exquisite control of core stereochemical features, this synthesis highlights the unique ability of Larock cyclization to generate two strained ring systems. In one of those instances specific geometrical and conformational constraints guide regiochemistry; this allows for the use of an unprotected alkyne, rendering it catalytic in Pd, and providing a single atropisomeric outcome. At this juncture a definitive rationalization for the observed atroposelectivity is not apparent. The precise choreography of cyclization events on specific substrates were planned using plastic molecular models which supported the observed outcomes. Rapid access to key unnatural AA building blocks from inexpensive natural AAs is enabled by scalable C-H activation and decarboxylative coupling methods. Although nonstrategic from an efficiency standpoint, homologation is deliberately enlisted late-stage to install the lysine sidechain solely for medicinal chemistry explorations of this portion of the molecule. For the same reasons, a late-stage incorporation of the C-terminus dipeptide was pursued. The atroposelective and modular synthesis of 1 sets the stage for the generation of analogs that are currently unavailable through engineered biosynthetic approaches and enables future exploration of the potent antibiotic activity of this important family of peptidic natural products.