As previously mentioned, among the natural products isolated to date, only four are known to possess the Tyr C-6-to-Trp N-1' linkage: lapparbin (1), neopetromin (2), tryptorubins, and nocapeptin A. Among these, the construction and total synthesis of the Tyr C-6-to-Trp N-1' linkage in tryptorubins, employing CuI-catalyzed intramolecular Ullmann coupling as the key reaction, were reported solely by Baran et al. in 2020. Given this context, the successful construction of the highly strained Tyr C-6-to-Trp N-1' linkage (cyclized products 25/28) on a decagram scale via Larock macrocyclization and the total synthesis of lapparbin (1) provide a novel strategic approach for the synthesis of various structurally complex RiPPs.