Late-Stage Native Peptide Modification Approach to the Total Synthesis of Koshidacins A and B

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Abstract
Herein, the total synthesis of the antimalarial natural products, koshidacins A and B, is disclosed. We developed an inverse peptide elongation sequence to elaborate the linear tetrapeptide by leveraging a soluble hydrophobic tag (TCbz group) for liquid-phase peptide synthesis. The key advances involve head-to-tail macrocyclization to provide the carrier-supported cyclic tetrapeptide and photoinduced deaminative alkylation to edit the native peptide residue that enabled us to construct the requisite alkyl chain in this unique natural product family.
Funding Information
  • Japan Agency for Medical Research and Development (JP25ama121035)
  • Japan Society for the Promotion of Science (23K06197)
  • Japan Society for the Promotion of Science (24K18256)
  • Japan Society for the Promotion of Science (25K09877)
  • Japan Society for the Promotion of Science (JP23H04884)
  • Japan Society for the Promotion of Science (JP24H01789)

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