(1) By utilizing C-H biarylation and Larock macrocyclization, a modular approach was developed to directly introduce biaryl moieties into amino acid residues. This represents a novel and generalizable method for constructing the highly strained Tyr C-6-to-Trp N-1' linkage on a decagram scale, extending beyond the single instance previously reported by Baran et al. using CuImediated Ullmann coupling. (2) The cyclized products 25/28 (atropisomer mixture 1:1) obtained through Larock macrocyclization were shown to undergo atropisomer convergence during the subsequent conversion to lapparbin (1). This finding elucidates that both compounds 25 and 28 are converted into lapparbin (1), enabling the scalable supply of lapparbin (1) without loss of the Larock cyclized intermediates. (3) The modular synthesis leveraging C-H biarylation and Larock macrocyclization discovered in the total synthesis of lapparbin (1) was demonstrated to be applicable to a variety of biaryl linkages. Additionally, this strategy was effective in constructing highly strained fluoro-lapparbin core structures, ensuring scalable production.