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Issue 5, 2019
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Diastereoselective synthesis of 3,3-disubstituted 3-nitro-4-chromanone derivatives as potential antitumor agents

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Abstract

We report an efficient and highly diastereoselective protocol for the rapid construction of 3-nitro substituted 4-chromanones by an intramolecular Michael-type cyclization of α-nitro aryl ketones bearing unsaturated ester units. A catalytic amount of KOtBu was found to be crucial for the high diastereoselective control of this transformation. With this protocol, a series of 3,3-disubstituted 3-nitro-4-chromanones were synthesized in good to excellent yields with high diastereoselectivities and showed moderate to good in vitro antitumor activities, representing promising antitumor hits for further drug discovery.

Graphical abstract: Diastereoselective synthesis of 3,3-disubstituted 3-nitro-4-chromanone derivatives as potential antitumor agents

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Publication details

The article was received on 06 Nov 2018, accepted on 26 Dec 2018 and first published on 07 Jan 2019


Article type: Communication
DOI: 10.1039/C8OB02761G
Citation: Org. Biomol. Chem., 2019,17, 1062-1066

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    Diastereoselective synthesis of 3,3-disubstituted 3-nitro-4-chromanone derivatives as potential antitumor agents

    H. Chen, J. Xie, D. Xing, J. Wang, J. Tang, Z. Yi, F. Xia, W. Qiu and F. Yang, Org. Biomol. Chem., 2019, 17, 1062
    DOI: 10.1039/C8OB02761G

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