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1 results on '"Isamu Shiina"'

1. 4‑(Dimethylamino)pyridine N‑Oxide-Catalyzed Macrolactamization Using 2‑Methyl-6-nitrobenzoic Anhydride in the Synthesis of the Depsipeptidic Analogue of FE399

Author

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

Subjects
General Chemical Engineering, Pyridine-N-oxide, 2-Methyl-6-nitrobenzoic anhydride, General Chemistry, Medicinal chemistry, Article, Catalysis, chemistry.chemical_compound, Chemistry, chemistry, Hexafluorophosphate, Reagent, Pyridine, QD1-999
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.

Published
2021

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