Solid-Phase Total Synthesis of Plusbacin A 3 .
Kazuki TakashinaAkira KatsuyamaRintaro KaguchiKazuki YamamotoToyotaka SatoSatoshi TakahashiMotohiro HoriuchiShin-Ichi YokotaSatoshi IchikawaPublished in: Organic letters (2022)
The total synthesis of the depsipeptide natural product plusbacin A 3 ( 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 A 3 ( 1 ).