Enantioselective Synthesis of Photodynamic Rubellin Anthraquinone Dimers

• Applicant: Dr. Vincent Eschenbrenner-Lux
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation ; Biological and Biomimetic Chemistry
• Term: from 2014 to 2017
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 270889223

The project covers the targeted syntheses of interesting dimeric anthraquinone natural products, the rubellins. The strategies developed for their formation are inspired from the informations obtained from their biosynthesis in the organisms they have been extracted from. The rubellins are a family of anthraquinone dimers that were isolated from a series of plant-parasitic fungi, and show potential antimicrobial and anticancer properties. The planned synthesis of this compound family includes the development of an atroposelective cross-coupling followed by an axial-to-point transferring dearomative photocyclization as key steps of the transformation. Subsequently, the synthesized compounds will be subjected to phenotypic screening under the influence of light to evaluate their photodynamic activity as chemical probes in biological systems. These compounds are potential chemical probes for the development of new photodynamic therapies, in the frame of prostate, ovary, and pancreas cancer research.

• DFG Programme: Research Fellowships
• International Connection: USA
• Host: Professor John A. Porco