Total Syntheses and Biological Evaluation of 3-O-Methylfunicone and Its Derivatives Prepared by TMPZnCl·LiCl-Mediated Halogenation and Carbonylative Stille Cross-Coupling

European Journal of Organic Chemistry, 2013, DOI: 10.1002/ejoc.201201256, Volume 2013, Issue 1, pages 77–83, published on 01.01.2013

European Journal of Organic Chemistry, online article

The total syntheses of the natural product 3-O-methylfunicone (1), a member of the funicone class of compounds, and its derivatives is reported. The key reactions in the construction of the biaryl ketone core are a regioselective TMPZnCl·LiCl halogenation and a carbonylative Stille cross-coupling reaction. In addition, the inhibitory activities of the funicones against Y-family DNA polymerase κ (pol κ) and polymerase η (pol η) were determined. We found that 1 and 12 exhibit inhibitory activity against pol η and 1 also against pol κ.

TU München
Helmholtz München
MPI of Neurobiology
MPI of Biochemistry