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Issue 9, 2016
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Traceless solid-phase α-hydroxytropolone synthesis

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α-Hydroxytropolones are established inhibitors of several therapeutically relevant binuclear metalloenzymes, and thus lead drug targets for various human diseases. We have leveraged a recently-disclosed three-component oxidopyrylium cycloaddition in the first solid-phase synthesis of α-hydroxytropolones. We also showed that, while minor impurities exist after cleavage and aqueous wash, the semi-crude products display activity in HIV RT-associated RNaseH enzymatic and cell-based assays consistent with pure molecules made in solution phase. These proof-of-principle studies demonstrate the feasibility of solid-phase α-hydroxytropolone synthesis and its potential to serve as a powerful platform for α-hydroxytropolone-based drug discovery and development.

Graphical abstract: Traceless solid-phase α-hydroxytropolone synthesis

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The article was received on 28 Apr 2016, accepted on 05 Jul 2016 and first published on 07 Jul 2016

Article type: Research Article
DOI: 10.1039/C6MD00237D
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Citation: Med. Chem. Commun., 2016,7, 1789-1792
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    Traceless solid-phase α-hydroxytropolone synthesis

    M. P. D'Erasmo, T. Masaoka, J. A. Wilson, E. M. Hunte, J. A. Beutler, S. F. J. Le Grice and R. P. Murelli, Med. Chem. Commun., 2016, 7, 1789
    DOI: 10.1039/C6MD00237D

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