In recent years, biaryl-containing peptides generated by cytochrome P450 macrocyclases have been reported in rapid succession worldwide. These natural products are known to possess various biaryl linkages within cyclic peptides. Many of these natural compounds, referred to as RiPPs (ribosomally synthesized and post-translationally modified peptides), not only feature challenging synthetic chemistry due to their atropisomeric axes but also exhibit either exceptionally potent biological activities or remain largely enigmatic in terms of their biological functions. Lapparbin (1) is a novel cyclic peptide isolated in 2023 by Oh and Kim et al. Structurally, it is characterized by an extremely rare and highly strained atrop-Tyr C-6-to-Trp N-1' linkage, composed of three amino acid residues: L-tyrosine, L-proline, and L-tryptophan. To date, among the natural products isolated, only four are known to contain the Tyr C-6-to-Trp N-1' linkage: lapparbin (1), neopetromin (2), tryptorubins, and nocapeptin A. Notably, the total synthesis of lapparbin (1), neopetromin (2), and nocapeptin A has not yet been reported. The sole reported instance for constructing the Tyr C-6-to-Trp N-1' linkage and the total synthesis of tryptorubins was reported by Baran et al. in 2020, utilizing intramolecular Ullmann coupling with CuI catalyst as the key reaction. Additionally, although some biological activity assays for lapparbin (1) have been conducted, its definitive biological activity remains unidentified. The synthetic plan for lapparbin (1) is depicted in Figure . The most challenging aspect of the total synthesis of lapparbin (1) is the construction of the highly strained atrop-Tyr C-6-to-Trp N-1' linkage, composed of three amino acid residues, inclucing Ltyrosine, L-proline, and L-tryptophan. Recently, we reported the total synthesis of cihunamide B, which features a highly strained atrop-Trp-Trp linkage. In this synthesis, the application of an SNAr reaction followed by atroposelective Larock macrocyclization enabled the construction of the highly strained atrop-Trp-Trp linkage. Hence, we hypothesized that this atroposelective Larock macrocyclization could be applied to the total synthesis of lapparbin (1). Additionally, the efficient introduction of biaryl moieties is a critical objective in this study. C-H activation has surfaced as an increasingly powerful method for directly introducing functional groups into inert and unfunctionalized positions. 8 These reactions are valuable for synthesizing non-natural amino acid derivatives. In recent years, various C-H activation reactions utilizing alanine derivatives have been reported. Aiming to achieve not only the total synthesis of lapparbin (1) but also a streamlined synthesis of non-natural analogues of lapparbin (1), we planned the total synthesis of lapparbin (1) through modular synthesis employing C-H biarylation of alanine derivatives. Specifically, we attempted the introduction of biaryl linkages via C-H biarylation of alanine derivatives using aminoquinoline as a directing group. 11 Furthermore, using subsequent Larock macrocyclization, we aimed to construct the highly strained atrop-Tyr-Trp linkage in a modular fashion. A distinguishing feature of this synthetic approach is its applicability to the introduction of arbitrary biaryl linkages, including non-natural biaryls, in a modular manner, extending beyond the synthesis of lapparbin (1).