An efficient and tunable route to AG7088, a rhinovirus protease inhibitor

Aldol reaction of N,N-dibenzyl valinal with propiolic acid ethyl ester derived lithium reagent provides anti-aminoalcohol 8 and syn-aminoalcohol 9, which are converted into the lactone 6 via two different routes. Alkylation of 6 followed by lactone ring opening afford the acid 2a, which is coupled w...

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Detalles Bibliográficos
Autores principales: Ma, Dawei, Xie, Weiqing, Zou, Bin, Lei, Qiong, Pei, Duanqing
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Elsevier Ltd. 2004
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7111835/
https://www.ncbi.nlm.nih.gov/pubmed/32287436
http://dx.doi.org/10.1016/j.tetlet.2004.08.179
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author Ma, Dawei
Xie, Weiqing
Zou, Bin
Lei, Qiong
Pei, Duanqing
author_facet Ma, Dawei
Xie, Weiqing
Zou, Bin
Lei, Qiong
Pei, Duanqing
author_sort Ma, Dawei
collection PubMed
description Aldol reaction of N,N-dibenzyl valinal with propiolic acid ethyl ester derived lithium reagent provides anti-aminoalcohol 8 and syn-aminoalcohol 9, which are converted into the lactone 6 via two different routes. Alkylation of 6 followed by lactone ring opening afford the acid 2a, which is coupled with the amine 3 and 5-methylisoxazole-3-carboxylate acid 1, respectively, to deliver AG7088.
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spelling pubmed-71118352020-04-02 An efficient and tunable route to AG7088, a rhinovirus protease inhibitor Ma, Dawei Xie, Weiqing Zou, Bin Lei, Qiong Pei, Duanqing Tetrahedron Lett Article Aldol reaction of N,N-dibenzyl valinal with propiolic acid ethyl ester derived lithium reagent provides anti-aminoalcohol 8 and syn-aminoalcohol 9, which are converted into the lactone 6 via two different routes. Alkylation of 6 followed by lactone ring opening afford the acid 2a, which is coupled with the amine 3 and 5-methylisoxazole-3-carboxylate acid 1, respectively, to deliver AG7088. Elsevier Ltd. 2004-10-18 2004-09-21 /pmc/articles/PMC7111835/ /pubmed/32287436 http://dx.doi.org/10.1016/j.tetlet.2004.08.179 Text en Copyright © 2004 Elsevier Ltd. All rights reserved. Since January 2020 Elsevier has created a COVID-19 resource centre with free information in English and Mandarin on the novel coronavirus COVID-19. The COVID-19 resource centre is hosted on Elsevier Connect, the company's public news and information website. Elsevier hereby grants permission to make all its COVID-19-related research that is available on the COVID-19 resource centre - including this research content - immediately available in PubMed Central and other publicly funded repositories, such as the WHO COVID database with rights for unrestricted research re-use and analyses in any form or by any means with acknowledgement of the original source. These permissions are granted for free by Elsevier for as long as the COVID-19 resource centre remains active.
spellingShingle Article
Ma, Dawei
Xie, Weiqing
Zou, Bin
Lei, Qiong
Pei, Duanqing
An efficient and tunable route to AG7088, a rhinovirus protease inhibitor
title An efficient and tunable route to AG7088, a rhinovirus protease inhibitor
title_full An efficient and tunable route to AG7088, a rhinovirus protease inhibitor
title_fullStr An efficient and tunable route to AG7088, a rhinovirus protease inhibitor
title_full_unstemmed An efficient and tunable route to AG7088, a rhinovirus protease inhibitor
title_short An efficient and tunable route to AG7088, a rhinovirus protease inhibitor
title_sort efficient and tunable route to ag7088, a rhinovirus protease inhibitor
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7111835/
https://www.ncbi.nlm.nih.gov/pubmed/32287436
http://dx.doi.org/10.1016/j.tetlet.2004.08.179
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