Total Synthesis

Our total synthesis programme is embedded in a strategic partnership with the Helmholtz Center of Infection Deseases (Braunschweig/Saarbrücken). Here, our activities include the structure elucidation of new biologically highly potent secondary metabolites, their total and semisynthesis followed by their biological and biomedical profiling. Many of these natural products show either antiproliferative or antibacterial activities. Selected examples are listed below.

Carolacton was isolated from Sorangium cellulosum and shows biofilm growth inhibition 0.005 µg/mL. Planktonic cultures are insensitive to Carolacton!

Structure elucidation: with T. Schmidt, M. Bock et al., Eur. J. Org. Chem. 2010, 1284-1289.

Total synthesis: with T. Schmidt, Angew. Chem. Int. Ed. 2012, 51, 1063–1066.

Biological activities: with T. Schmidt, J. Ammermann, Org. Biomol. Chem. 2015, 13, 5765 - 5774; with R. Müller, I. Wagner-Döbler, Scientific Rep. 2016, 6, article number 29677; with R. Müller, I. Wagner-Döbler, mSphere 2017, 2, e00375-17.

Elansolid A1 and A2 were isolated from gliding bacterium Chitinophaga. They show antibacterial activity (including Staphylococcus aureus and Micrococcus luteus)

Isolation and structure isolation:  with R. Dehn, N. Schläger, et al., Angew Chem. Int. Ed. 2011, 50, 532-536; with R. Dehn, R. Müller, et al., Chem. Eur. J. 2011, 17, 7739–7744.

Biosynthesis: with R. Dehn, A. Weber, et al. Angew. Chem. Int. Ed. 2011, 50, 3882-3887; with Steinmetz, R. Müller, et al., ChemBioChem 2012, 13, 1813-1817.

Total synthesis: with S. Weber, N. Schläger, R. Dehn, et al., Org. Lett. 2014, 16, 568–571 (highlighted in SynFacts); with L.-L. Wang, J. Herrmann, et al., Chem. Eur. J. 2017, 23, 5291 – 5298; with L.-L. Wang, Beilstein J. Org. Chem. 2017, 13, 1280–1287.

Cystobactamid 861-2 was isolated from Cystobacter sp. and possesses strong antibacterial activity. This compound is a inhibitor of bacterial topoisomerase.

Total synthesis: with T. Planke, M. Brönstrup, R. Müller, et al. Angew. Chem. Int. Ed. 2017, 56, 12760-12764; with T. Planke, F. Fohrer, R. Müller et al. Org. Lett. 2019, 21, 1359-1363.

Thuggacin A was isolated from myxobacterium Sorangium cellulosum and shows strong antibiotic activity (including Mycobacterium tuberculosis). It targets the bacterial respiratory chain.

Isolation and structure elucidation: with M. Bock et al., Angew. Chem. Int. Ed. 2008, 47, 2308-2311.

Total synthesis: with M. Bock, et al. Angew. Chem. Int. Ed. 2008, 47, 9134-9137.