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

Xiaotan Yu; Xiaoxia Gu; Yunpeng Zhao; Fengqing Wang; Weiguang Sun; Changxing Qi; Lianghu Gu; Yonghui Zhang

doi:10.1039/D2RA08133D

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

Xiaotan Yu,

‡^a Xiaoxia Gu,‡^a Yunpeng Zhao,^a Fengqing Wang,^a Weiguang Sun,^a Changxing Qi,*^a Lianghu Gu*^a and Yonghui Zhang

*^a

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* Corresponding authors

^a Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China
E-mail: zhangyh@mails.tjmu.edu.cn, gulianghu@hust.edu.cn, qichangxing@hust.edu.cn

Abstract

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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DOI: https://doi.org/10.1039/D2RA08133D
Article type: Paper
Submitted: 21 Dec 2022
Accepted: 30 Jan 2023
First published: 07 Feb 2023
This article is Open Access

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RSC Adv., 2023,13, 4859-4864

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

X. Yu, X. Gu, Y. Zhao, F. Wang, W. Sun, C. Qi, L. Gu and Y. Zhang, RSC Adv., 2023, 13, 4859 DOI: 10.1039/D2RA08133D

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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

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

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