New perspectives for Lewis acid-catalyzed [2+2] cycloadditions of allenoates

• Applicant: Professor Dr. Johannes M. Wahl
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2017 to 2019
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 361417940

The objective of this proposal is the synthesis of hebelophyllene E, a naturally occurring sesquiterpene, which was isolated from the ectomycorrhizal fungus Hebeloma longicaudum in the late 1990s. In the context of this project, we have developed an enantioselective Lewis-acid catalyzed [2+2] cycloaddition followed by a ligand controlled copper hydride reduction to access the cis-fused cyclobutane motif. Thus, the goal is to apply these findings in the synthesis of hebelophyllene E and demonstrate that our methodology can be used early in a synthetic sequence as well as late stage using highly functionalized alkenes.

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