The synthesis of cihunamide B (1) begins with the SNAr reaction of the inexpensive 1-bromo-3-fluoro-2-nitrobenzene 3 and N-Boc-L-tryptophan 2. 4 2 and the commercially available 1bromo-3-fluoro-2-nitrobenzene 3 were linked by the SNAr reaction by using NaOH in DMSO under room temperature to synthesize 7, a fragment essential for the intramolecular Larock indole synthesis. It is worth noting that the SNAr reaction was carried out on a 40-gram scale and 7 was quantitatively obtained from 2 in a single step without any side reactions such as racemization. It was found that the use of free carboxylic acid is important to prevent racemization. The resulting 7 was then treated with HCl/MeOH to deprotect the Boc group and promote the methyl esterification simultaneously, followed by amide coupling with 4 using HATU to afford 8 in 88% yield. The resulting 8 was converted to 9 in 89% by deprotection of the Boc group by HCl and subsequent amide coupling with 5 by HATU. It is worth noting that the C-N bond between the tryptophan and the aromatic ring in 9 was stable and no decomposition or other side reactions occurred from 7 several steps, including strongly acidic conditions.