Solid-Phase Total Synthesis of Plusbacin A 3

Solid-Phase Total Synthesis of Plusbacin A 3

The total synthesis of the depsipeptide natural product plusbacin A ( ) 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...

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Veröffentlicht in:Organic letters 2022-03, Vol.24 (11), p.2253-2257
Hauptverfasser: Takashina, Kazuki, Katsuyama, Akira, Kaguchi, Rintaro, Yamamoto, Kazuki, Sato, Toyotaka, Takahashi, Satoshi, Horiuchi, Motohiro, Yokota, Shin-Ichi, Ichikawa, Satoshi
Format: Artikel
Sprache:eng
Schlagworte:
Depsipeptides
Hydrolysis
Solid-Phase Synthesis Techniques
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Zusammenfassung:The total synthesis of the depsipeptide natural product plusbacin A ( ) 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 ( ).
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c00667