Solid-Phase Total Synthesis of Plusbacin A<sub>3</sub>
Kazuki Takashina, Akira Katsuyama, Rintaro Kaguchi, Kazuki Yamamoto, Toyotaka Sato, Satoshi Takahashi, Motohiro Horiuchi, Shin‐ichi Yokota, Satoshi Ichikawa
Abstract
The total synthesis of the depsipeptide natural product plusbacin A3 (1) utilizing solid-phase peptide synthesis (SPPS) was disclosed. A 3-hydroxy-proline derivative compatible with Fmoc SPPS was prepared by a diastereoselective Joullié–Ugi three-component reaction (JU-3CR)/hydrolysis sequence. After peptide elongation on the solid support, cleavage of the peptide from the resin, followed by macrolactamization and global deprotection, gave plusbacin A3 (1).
Topics & Concepts
ChemistrySolid-phase synthesisDepsipeptideTotal synthesisPeptide synthesisPeptideCleavage (geology)Derivative (finance)HydrolysisCombinatorial chemistryNatural productStereochemistryResidue (chemistry)ElongationPhase (matter)Organic chemistryBiochemistryUltimate tensile strengthGeotechnical engineeringMaterials scienceEngineeringMetallurgyFinancial economicsFracture (geology)EconomicsChemical Synthesis and AnalysisBiochemical and Structural CharacterizationAntimicrobial Peptides and Activities