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

[Image: see text] 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...

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Autores principales: Tonoi, Takayuki, Inohana, Takehiko, Kawahara, Ryo, Sato, Teruyuki, Ikeda, Miyuki, Akutsu, Miku, Murata, Takatsugu, Shiina, Isamu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7876680/
https://www.ncbi.nlm.nih.gov/pubmed/33585740
http://dx.doi.org/10.1021/acsomega.0c04878
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author Tonoi, Takayuki
Inohana, Takehiko
Kawahara, Ryo
Sato, Teruyuki
Ikeda, Miyuki
Akutsu, Miku
Murata, Takatsugu
Shiina, Isamu
author_facet Tonoi, Takayuki
Inohana, Takehiko
Kawahara, Ryo
Sato, Teruyuki
Ikeda, Miyuki
Akutsu, Miku
Murata, Takatsugu
Shiina, Isamu
author_sort Tonoi, Takayuki
collection PubMed
description [Image: see text] 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.
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spelling pubmed-78766802021-02-12 4-(Dimethylamino)pyridine N-Oxide-Catalyzed Macrolactamization Using 2-Methyl-6-nitrobenzoic Anhydride in the Synthesis of the Depsipeptidic Analogue of FE399 Tonoi, Takayuki Inohana, Takehiko Kawahara, Ryo Sato, Teruyuki Ikeda, Miyuki Akutsu, Miku Murata, Takatsugu Shiina, Isamu ACS Omega [Image: see text] 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. American Chemical Society 2021-01-11 /pmc/articles/PMC7876680/ /pubmed/33585740 http://dx.doi.org/10.1021/acsomega.0c04878 Text en © 2021 The Authors. Published by American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.
spellingShingle Tonoi, Takayuki
Inohana, Takehiko
Kawahara, Ryo
Sato, Teruyuki
Ikeda, Miyuki
Akutsu, Miku
Murata, Takatsugu
Shiina, Isamu
4-(Dimethylamino)pyridine N-Oxide-Catalyzed Macrolactamization Using 2-Methyl-6-nitrobenzoic Anhydride in the Synthesis of the Depsipeptidic Analogue of FE399
title 4-(Dimethylamino)pyridine N-Oxide-Catalyzed Macrolactamization Using 2-Methyl-6-nitrobenzoic Anhydride in the Synthesis of the Depsipeptidic Analogue of FE399
title_full 4-(Dimethylamino)pyridine N-Oxide-Catalyzed Macrolactamization Using 2-Methyl-6-nitrobenzoic Anhydride in the Synthesis of the Depsipeptidic Analogue of FE399
title_fullStr 4-(Dimethylamino)pyridine N-Oxide-Catalyzed Macrolactamization Using 2-Methyl-6-nitrobenzoic Anhydride in the Synthesis of the Depsipeptidic Analogue of FE399
title_full_unstemmed 4-(Dimethylamino)pyridine N-Oxide-Catalyzed Macrolactamization Using 2-Methyl-6-nitrobenzoic Anhydride in the Synthesis of the Depsipeptidic Analogue of FE399
title_short 4-(Dimethylamino)pyridine N-Oxide-Catalyzed Macrolactamization Using 2-Methyl-6-nitrobenzoic Anhydride in the Synthesis of the Depsipeptidic Analogue of FE399
title_sort 4-(dimethylamino)pyridine n-oxide-catalyzed macrolactamization using 2-methyl-6-nitrobenzoic anhydride in the synthesis of the depsipeptidic analogue of fe399
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7876680/
https://www.ncbi.nlm.nih.gov/pubmed/33585740
http://dx.doi.org/10.1021/acsomega.0c04878
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