Name: Julia Kerschbaumer (geb. Leuger)
Diploma / M.Sc degree: Westfälische Wilhelms-Universität Münster, Germany
(March 2005)
Title: Total synthesis of 16,19-cis-murisolin


Homepage: www.uni-muenster.de/Chemie.oc/research/hau/personen/leuger.htm

Abstract of Research Project

The annonaceous acetogenins are a relatively new class of natural products. In 1982 the first annonaceous acetogenin, uvaricin, was isolated from Uvaria accuminata, a plant belonging to the mainly tropical Annonaceae species. Since then, more than 400 members of this class have been identified to date, which makes the annonaceous acetogenins one of the most rapidly growing classes of new natural compounds.

The acetogenins arouse great interest, due to their broad range of biological properties. They offer anthelmintic, in vivo and cytotoxic antitumor, antimalarial, antiprotozoal and pesticidal activities. The common structure of these promising new chemotypes for antitumor and pesticidal agents is most often characterized by an unbranched C₃₂ or C₃₄ fatty acid ending in a g-lactone. Spread along the alkyl chain there are usually one, two or three tetrahydrofuran rings and several other oxygenated functions such as hydroxyl, carbonyl or epoxy groups.

16,19-cis-Murisolin, the target molecule of my thesis, was isolated in 1995 for the first time from the seeds of Asimina triloba. Like two of its naturally occuring diastereoisomers, 16,19-cis-murisolin shows strong cytotoxicity against six human tumor cell lines, what makes it for us an interesting aim of a total synthesis.

In the field of total syntheses of annonaceous acetogenins many efforts have already been made. The synthetic route we are planning, initially for the compound 16,19-cis-murisolin, follows a new strategy that should enable us to produce with only minor modifications in the reaction procedure a range of different acetogenins with defined stereochemistry.


Publications

P. Persich, J. Kerschbaumer, S. Helling, B. Hildmann, B. Wibbeling, G. Haufe
Transannular O–Heterocyclization: A Useful Tool for the Total Synthesis of Murisolin and 16,19-cis-Murisolin
Org. Lett. 14(22) (2012), 5628–5631.

J. Leuger, G. Blond, T. Billard, G. Haufe, B.R. Langlois
1,4-Addition of Electron-rich Heterocycles onto beta-Perfluoroalkyl Enones
J. Fluorine Chem. 132 (2011), 799-803.


Julia Leuger
eMail: Julia Leuger