Cyctetryptomycin A and B (1-2) (Figure ) are tetrameric natural products that were isolated in 2021. These intriguing compounds are characterized by the complex linkage of four naturally occurring tryptophans into an unprecedentedly complex macrocyclic molecule. These natural products possess neuroprotective activity and are expected to be effective in treating neurodegenerative diseases such as ALS (amyotrophic lateral sclerosis), Alzheimer's, and Parkinson's diseases. However, the total synthesis of cyctetryptomycin A and B (1-2) has not yet been reported. In the present study, we developed a Zr-catalyzed scalable C3-C3 dimerization of tryptophan derivative and CttpCcatalyzed oxidative coupling of tryptophan and successfully prepared cyctetryptomycin A and B (1-2) in 8 steps. Our synthetic method is expected to contribute to the development of potential therapeutic agents for neurodegenerative diseases such as ALS, Alzheimer's, and Parkinson's diseases.