In conclusion, we have developed the first total synthesis of antibacterial cihunamide B (1). This work features (1) the formation of a C-N bond between N-Boc-L-tryptophan 2 and 1bromo-3-fluoro-2-nitrobenzene 3 on a decagram scale utilizing inexpensive reagents through the SNAr reaction, and ( ) the synthesis of a highly strained cyclic peptide by atroposelective Larock macrocyclization, resulting in the successful production of protected cihunamide 17 on a 3.6 g scale. Additionally, this synthetic pathway obviates the need for specialized apparatus or reagents, enabling the large-scale synthesis of protected cihunamide 17 using economical starting materials and readily accessible reagents. This development is anticipated to have farreaching implications in biological research and related disciplines. Moreover, the utilization of protected cihunamide 17 allows for the possibility of conducting structure-activity relationship (SAR) studies.