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Synthesis of monoalkylidene diketopiperazines and application to the synthesis of barettin

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Abstract

The synthesis of barettin, a selective serotonin receptor inhibitor and potent antibiofouling natural product, is described. The synthesis starts with the diketopiperazine nucleus intact and the side chains are installed using iterative aldol condensations. The route represents a general strategy for synthesis of a wide array of mono-alkylidene diketopiperazine structures, including those derived from non-canonical amino acid residues.

Graphical abstract: Synthesis of monoalkylidene diketopiperazines and application to the synthesis of barettin

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Publication details

The article was received on 13 Sep 2017, accepted on 28 Sep 2017 and first published on 05 Oct 2017


Article type: Paper
DOI: 10.1039/C7OB02297B
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Synthesis of monoalkylidene diketopiperazines and application to the synthesis of barettin

    E. W. Kelley, S. G. Norman and J. R. Scheerer, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB02297B

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