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Triphosgene-Mediated Couplings in the Solid Phase: Total Synthesis of Brachystemin A

Lijing Fang,Chunlei Wu,Zaidan Yu,Peng Shang,Yongxian Cheng,Yuefeng Peng,Wu Su

Graphical A highly efficient protocol for the triphosgene-mediated solid-phase coupling of proteinogenic amino acids is developed and applied to the first total synthesis of the bioactive natural octacyclopeptide brachystemin A. A reproducible, highly efficient, and racemization-free protocol for the triphosgene-mediated solid-phase coupling of proteinogenic amino acids was developed. The efficiency of the reaction was demonstrated by the first total synthesis of the bioactive natural octacyclopeptide brachystemin A. This protocol will broaden the application of triphosgene in the synthesis of a wide range of peptides, including aromatic amino acids, N -alkylated amino acids, as well as proteinogenic amino acids.