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Issue 5, 2012
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Thiolation of symmetrical and unsymmetrical diketopiperazines

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Abstract

The introduction of sulfur units into a variety of symmetrical and unsymmetrical diketopiperazines (DKPs) is described. We investigated different thiolation methods utilizing several bases and electrophilic sulfur reagents, leading to monomethylthio-, bis(methylthio)-, and epithio-DKPs. Their formation proceeded diastereoselectively, facilitating the application in total syntheses of many thiodiketopiperazine (TDKP) natural products. Furthermore, possible side reactions as well as mechanistic studies and stereochemical structural assignments of the obtained products are given.

Graphical abstract: Thiolation of symmetrical and unsymmetrical diketopiperazines

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Publication details

The article was received on 01 Oct 2011, accepted on 28 Nov 2011 and first published on 30 Nov 2011


Article type: Communication
DOI: 10.1039/C2OB06663G
Citation: Org. Biomol. Chem., 2012,10, 935-940

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    Thiolation of symmetrical and unsymmetrical diketopiperazines

    B. M. Ruff, S. Zhong, M. Nieger and S. Bräse, Org. Biomol. Chem., 2012, 10, 935
    DOI: 10.1039/C2OB06663G

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