Development of Iridium-catalyzed, intramolecular, asymmetric allylic alkylation reactions and their application towards the total synthesis of Aquilarabietic Acid H

• Applicant: Dr. Sebastian Lackner
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2017 to 2019
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 390789510

Synthetic organic chemistry continues to be of highest importance within drug discovery and development, as well as medicinal chemistry. This led to increased interest in catalytic, enantioselective synthesis in recent years, particularly regarding difficult to access, quaternary stereocenters. Based on previous initial studies the research project will initially focus on developing an Iridium-catalyzed, intramolecular, asymmetric allylic alkylation reaction of 1,3-dicarbonyls. This would allow easy access to various carbocycles with vicinal quaternary-tertiary stereocenters. This new methodology is then to be applied to the total synthesis of Aquilarabietic Acid H, a novel natural compound that showed anti-depressant properties in initial studies. Further, the asymmetric, intramolecular reaction is then to be extended to substrates with carbocycle-containing allyl moieties. This would give easy access to polycyclic motifs commonly found in steroids and related pharmaceutical drugs.

• DFG Programme: Research Fellowships
• International Connection: USA
• Host: Professor Brian M. Stoltz, Ph.D.