Oxidative Cyclization at ortho-Position of Phenol: Improved Total Synthesis of 3-(Phenethylamino)demethyl(oxy)aaptamine

A shorter synthesis of the demethyl(oxy)aaptamine skeleton was developed via oxidative intramolecular cyclization of 1-(2-azidoethyl)-6-methoxyisoquinolin-7-ol followed by dehydrogenation with a hypervalent iodine reagent. This is the first example of oxidative cyclization at the ortho-position of p...

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Autores principales: Nakatani, Yuki, Kimura, Risa, Kimata, Tomoyo, Kotoku, Naoyuki
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10221624/
https://www.ncbi.nlm.nih.gov/pubmed/37233505
http://dx.doi.org/10.3390/md21050311
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author Nakatani, Yuki
Kimura, Risa
Kimata, Tomoyo
Kotoku, Naoyuki
author_facet Nakatani, Yuki
Kimura, Risa
Kimata, Tomoyo
Kotoku, Naoyuki
author_sort Nakatani, Yuki
collection PubMed
description A shorter synthesis of the demethyl(oxy)aaptamine skeleton was developed via oxidative intramolecular cyclization of 1-(2-azidoethyl)-6-methoxyisoquinolin-7-ol followed by dehydrogenation with a hypervalent iodine reagent. This is the first example of oxidative cyclization at the ortho-position of phenol that does not involve spiro-cyclization, resulting in the improved total synthesis of 3-(phenethylamino)demethyl(oxy)aaptamine, a potent anti-dormant mycobacterial agent.
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spelling pubmed-102216242023-05-28 Oxidative Cyclization at ortho-Position of Phenol: Improved Total Synthesis of 3-(Phenethylamino)demethyl(oxy)aaptamine Nakatani, Yuki Kimura, Risa Kimata, Tomoyo Kotoku, Naoyuki Mar Drugs Article A shorter synthesis of the demethyl(oxy)aaptamine skeleton was developed via oxidative intramolecular cyclization of 1-(2-azidoethyl)-6-methoxyisoquinolin-7-ol followed by dehydrogenation with a hypervalent iodine reagent. This is the first example of oxidative cyclization at the ortho-position of phenol that does not involve spiro-cyclization, resulting in the improved total synthesis of 3-(phenethylamino)demethyl(oxy)aaptamine, a potent anti-dormant mycobacterial agent. MDPI 2023-05-19 /pmc/articles/PMC10221624/ /pubmed/37233505 http://dx.doi.org/10.3390/md21050311 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Nakatani, Yuki
Kimura, Risa
Kimata, Tomoyo
Kotoku, Naoyuki
Oxidative Cyclization at ortho-Position of Phenol: Improved Total Synthesis of 3-(Phenethylamino)demethyl(oxy)aaptamine
title Oxidative Cyclization at ortho-Position of Phenol: Improved Total Synthesis of 3-(Phenethylamino)demethyl(oxy)aaptamine
title_full Oxidative Cyclization at ortho-Position of Phenol: Improved Total Synthesis of 3-(Phenethylamino)demethyl(oxy)aaptamine
title_fullStr Oxidative Cyclization at ortho-Position of Phenol: Improved Total Synthesis of 3-(Phenethylamino)demethyl(oxy)aaptamine
title_full_unstemmed Oxidative Cyclization at ortho-Position of Phenol: Improved Total Synthesis of 3-(Phenethylamino)demethyl(oxy)aaptamine
title_short Oxidative Cyclization at ortho-Position of Phenol: Improved Total Synthesis of 3-(Phenethylamino)demethyl(oxy)aaptamine
title_sort oxidative cyclization at ortho-position of phenol: improved total synthesis of 3-(phenethylamino)demethyl(oxy)aaptamine
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10221624/
https://www.ncbi.nlm.nih.gov/pubmed/37233505
http://dx.doi.org/10.3390/md21050311
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