The ability to modularly introduce various biaryl linkages in the total synthesis of lapparbin (1) is a major advantage of this synthetic strategy. Consequently, a highly strained fluoro linkage was constructed using the fluorine-substituted biaryl linkage 39 (Figure ). Compound 39 underwent protection of the aminoquinoline and aniline NH groups with Boc, followed by solvolysis with MeOH and Boc deprotection, yielding compound 40 in 82% (3 steps). Compound 40 was then converted to the Larock macrocyclization precursor 41 using a methodology similar to the total synthesis pathway of lapparbin (1). Subsequent Larock macrocyclization of precursor 41 with Pd(tBu3P)2 and DIPEA in PhMe at 110 °C yielded the highly strained fluorolapparbin core structure (43) with an isolated yield of 65%, producing 700 mg of the desired compound. The atroposelectivity of this reaction was approximately 1:1, akin to the Larock macrocyclization in the total synthesis of lapparbin (1).