Collective synthesis of aspulvinone and its analogues by vinylogous aldol condensation of substituted tetronic acids with aldehydes

A mild, modular and efficient synthetic method with broad substrate scope was developed for aspulvinones. Nine natural aspulvinones were synthesized, six of which were for the first time. The aldol condensation delivered Z-configuration products predominantly in MeCN. Meanwhile, alkoxy exchange occu...

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Autores principales: Yu, Xiaotan, Gu, Xiaoxia, Zhao, Yunpeng, Wang, Fengqing, Sun, Weiguang, Qi, Changxing, Gu, Lianghu, Zhang, Yonghui
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2023
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9903353/
https://www.ncbi.nlm.nih.gov/pubmed/36760298
http://dx.doi.org/10.1039/d2ra08133d
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author Yu, Xiaotan
Gu, Xiaoxia
Zhao, Yunpeng
Wang, Fengqing
Sun, Weiguang
Qi, Changxing
Gu, Lianghu
Zhang, Yonghui
author_facet Yu, Xiaotan
Gu, Xiaoxia
Zhao, Yunpeng
Wang, Fengqing
Sun, Weiguang
Qi, Changxing
Gu, Lianghu
Zhang, Yonghui
author_sort Yu, Xiaotan
collection PubMed
description A mild, modular and efficient synthetic method with broad substrate scope was developed for aspulvinones. Nine natural aspulvinones were synthesized, six of which were for the first time. The aldol condensation delivered Z-configuration products predominantly in MeCN. Meanwhile, alkoxy exchange occurred in MeOH and EtOH. Aspulvinone O and E, and substrate 49, 50, and 51 exhibited modest anti-SARS-CoV-2 activity in a high-throughput screening and enzyme kinetics assay.
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spelling pubmed-99033532023-02-08 Collective synthesis of aspulvinone and its analogues by vinylogous aldol condensation of substituted tetronic acids with aldehydes Yu, Xiaotan Gu, Xiaoxia Zhao, Yunpeng Wang, Fengqing Sun, Weiguang Qi, Changxing Gu, Lianghu Zhang, Yonghui RSC Adv Chemistry A mild, modular and efficient synthetic method with broad substrate scope was developed for aspulvinones. Nine natural aspulvinones were synthesized, six of which were for the first time. The aldol condensation delivered Z-configuration products predominantly in MeCN. Meanwhile, alkoxy exchange occurred in MeOH and EtOH. Aspulvinone O and E, and substrate 49, 50, and 51 exhibited modest anti-SARS-CoV-2 activity in a high-throughput screening and enzyme kinetics assay. The Royal Society of Chemistry 2023-02-07 /pmc/articles/PMC9903353/ /pubmed/36760298 http://dx.doi.org/10.1039/d2ra08133d Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Yu, Xiaotan
Gu, Xiaoxia
Zhao, Yunpeng
Wang, Fengqing
Sun, Weiguang
Qi, Changxing
Gu, Lianghu
Zhang, Yonghui
Collective synthesis of aspulvinone and its analogues by vinylogous aldol condensation of substituted tetronic acids with aldehydes
title Collective synthesis of aspulvinone and its analogues by vinylogous aldol condensation of substituted tetronic acids with aldehydes
title_full Collective synthesis of aspulvinone and its analogues by vinylogous aldol condensation of substituted tetronic acids with aldehydes
title_fullStr Collective synthesis of aspulvinone and its analogues by vinylogous aldol condensation of substituted tetronic acids with aldehydes
title_full_unstemmed Collective synthesis of aspulvinone and its analogues by vinylogous aldol condensation of substituted tetronic acids with aldehydes
title_short Collective synthesis of aspulvinone and its analogues by vinylogous aldol condensation of substituted tetronic acids with aldehydes
title_sort collective synthesis of aspulvinone and its analogues by vinylogous aldol condensation of substituted tetronic acids with aldehydes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9903353/
https://www.ncbi.nlm.nih.gov/pubmed/36760298
http://dx.doi.org/10.1039/d2ra08133d
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