Efficient total synthesis of leiodermatolide

• Applicant: Dr. Julian Wippich
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: Funded in 2017
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 372789477

This project concerns with the efficient total synthesis of leiodermatolide. This polyketide has been proven to be very effective against various cancer cell lines. Due to the limitation by isolation from nature and rather long previous total syntheses, we propose a significantly shorter and convergent synthesis of this unique natural product. By applying recently developed transition metal catalyzed processes, we will be able to shorten the number of steps significantly. The synthesis is divided into two fragment. After recent completion of the eastern fragment in the Krische laboratory, this project now focuses on the western fragment and the completion of the natural product. Whereas new state of the art transformation, like the ruthenium catalyzed syn-crotylation or the rhodium catalyzed Z-dienylation, will be employed. The union of the two fragment will be conducted through a Yamaguchi esterification and olefin metathesis. After completion, we hope to synthesis reasonable quantities of this potential drug candidate to evaluate the unique mode of action in biological tests.

• DFG Programme: Research Fellowships
• International Connection: USA
• Host: Professor Dr. Michael J. Krische