Issue 40, 2017

Synthesis of monoalkylidene diketopiperazines and application to the synthesis of barettin

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

Supplementary files

Article information

Article type
Paper
Submitted
13 Sep 2017
Accepted
28 Sep 2017
First published
05 Oct 2017

Org. Biomol. Chem., 2017,15, 8634-8640

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, 15, 8634 DOI: 10.1039/C7OB02297B

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