4-(Dimethylamino)pyridine N-Oxide-Catalyzed Macrolactamization Using 2-Methyl-6-nitrobenzoic Anhydride in the Synthesis of the Depsipeptidic Analogue of FE399

Takayuki Tonoi, Takehiko Inohana, Ryo Kawahara, Teruyuki Sato, Miyuki Ikeda, Miku Akutsu, Takatsugu Murata, Isamu Shiina

Research output: Contribution to journalArticlepeer-review

Abstract

A depsipeptidic analogue of FE399 was efficiently synthesized mainly through macrolactamization using 2-methyl-6-nitrobenzoic anhydride (MNBA), and a detailed investigation of the desired 16-membered macrolactam core of FE399 was performed. It was determined that the combination of MNBA and a catalytic amount of 4-(dimethylamino)pyridine N-oxide exhibits much higher activity than that of conventionally used coupling reagents such as hexafluorophosphate azabenzotriazole tetramethyl uronium and benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate.

Original languageEnglish
Pages (from-to)3571-3577
Number of pages7
JournalACS Omega
Volume6
Issue number5
DOIs
Publication statusPublished - 9 Feb 2021

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