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Issue 62, 2015
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The amido-pentadienoate-functionality of the rakicidins is a thiol reactive electrophile – development of a general synthetic strategy

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Abstract

We demonstrate that a unique class-defining functionality (mc-APD) found in macrocyclic natural products with potent anti-cancer activity, imparts these compounds with electrophilic reactivity. The mc-APD group represents an interesting structural hybrid between canonical biologically relevant Michael-acceptors. Further, a novel thiol-elimination method for preparation of the mc-APD group is outlined.

Graphical abstract: The amido-pentadienoate-functionality of the rakicidins is a thiol reactive electrophile – development of a general synthetic strategy

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Publication details

The article was received on 01 Jun 2015, accepted on 30 Jun 2015 and first published on 30 Jun 2015


Article type: Communication
DOI: 10.1039/C5CC04500B
Author version available: Download Author version (PDF)
Citation: Chem. Commun., 2015,51, 12427-12430
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    The amido-pentadienoate-functionality of the rakicidins is a thiol reactive electrophile – development of a general synthetic strategy

    L. L. Clement, M. Tsakos, E. S. Schaffert, C. Scavenius, J. J. Enghild and T. B. Poulsen, Chem. Commun., 2015, 51, 12427
    DOI: 10.1039/C5CC04500B

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