Issue 5, 2012

Thiolation of symmetrical and unsymmetrical diketopiperazines

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

Supplementary files

Article information

Article type
Communication
Submitted
01 Oct 2011
Accepted
28 Nov 2011
First published
30 Nov 2011

Org. Biomol. Chem., 2012,10, 935-940

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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