An Expedient Total Synthesis of Triciribine

In the present paper, we report an expedient total synthesis of triciribine, a tricyclic 7-deazapurine nucleoside and protein kinase B (AKT ) inhibitor, in 35% overall yield. Our synthesis route features a highly regioselective substitution of 1-N-Boc-2-methylhydrazine and a trifluoroacetic acid cat...

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Autores principales: Hu, Chen, Ruan, Zhizhong, Ding, Haixin, Zhou, Yirong, Xiao, Qiang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6154533/
https://www.ncbi.nlm.nih.gov/pubmed/28420174
http://dx.doi.org/10.3390/molecules22040643
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author Hu, Chen
Ruan, Zhizhong
Ding, Haixin
Zhou, Yirong
Xiao, Qiang
author_facet Hu, Chen
Ruan, Zhizhong
Ding, Haixin
Zhou, Yirong
Xiao, Qiang
author_sort Hu, Chen
collection PubMed
description In the present paper, we report an expedient total synthesis of triciribine, a tricyclic 7-deazapurine nucleoside and protein kinase B (AKT ) inhibitor, in 35% overall yield. Our synthesis route features a highly regioselective substitution of 1-N-Boc-2-methylhydrazine and a trifluoroacetic acid catalyzed one-pot transformation which combined the deprotection of the tert-butylcarbonyl (Boc) group and ring closure reaction together to give a tricyclic nucleobase motif.
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spelling pubmed-61545332018-11-13 An Expedient Total Synthesis of Triciribine Hu, Chen Ruan, Zhizhong Ding, Haixin Zhou, Yirong Xiao, Qiang Molecules Communication In the present paper, we report an expedient total synthesis of triciribine, a tricyclic 7-deazapurine nucleoside and protein kinase B (AKT ) inhibitor, in 35% overall yield. Our synthesis route features a highly regioselective substitution of 1-N-Boc-2-methylhydrazine and a trifluoroacetic acid catalyzed one-pot transformation which combined the deprotection of the tert-butylcarbonyl (Boc) group and ring closure reaction together to give a tricyclic nucleobase motif. MDPI 2017-04-17 /pmc/articles/PMC6154533/ /pubmed/28420174 http://dx.doi.org/10.3390/molecules22040643 Text en © 2017 by the authors. 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 (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Hu, Chen
Ruan, Zhizhong
Ding, Haixin
Zhou, Yirong
Xiao, Qiang
An Expedient Total Synthesis of Triciribine
title An Expedient Total Synthesis of Triciribine
title_full An Expedient Total Synthesis of Triciribine
title_fullStr An Expedient Total Synthesis of Triciribine
title_full_unstemmed An Expedient Total Synthesis of Triciribine
title_short An Expedient Total Synthesis of Triciribine
title_sort expedient total synthesis of triciribine
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6154533/
https://www.ncbi.nlm.nih.gov/pubmed/28420174
http://dx.doi.org/10.3390/molecules22040643
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