Synthesis of the Core Structure of Sungeidine Natural Products

• Applicant: Dr. Martin Petzold
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2021 to 2022
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 458642402

In the course of the project, a synthetic route to access the core of sungeidine natural products is intended. Sungeidines are a class of secondary metabolites generated by microbial biosynthetic gene clusters from ene-diynes. Because related biosynthetic ene-diyne precursors of the dynemicin-type possess interesting pharmacological properties, secondary metabolites of such are thought to potentially exhibit novel bioactive characteristics too.As key step, a novel (4+2)-cycloaddition (Diels-Alder reaction) will be developed, for which in-situ generated and to this date underexplored oxopyrrolium ions shall be reacted with activated dienes. Their in-situ generation will rely on photo- or electrochemical approaches, in which dihydropyrrol-2-ones serve as predecessors. In addition, a new synthetic strategy to access (oligo)substituted pyrrolidinones, which represent common heterocyclic motifs found in a large variety of compound classes, can be achieved.Once the synthetic strategy’s feasibility for the synthesis of the sungeidine core has been proven, alterations of the different starting materials allow the synthesis of different sungeidines.

• DFG Programme: WBP Fellowship
• International Connection: USA
• Host: Professor Richmond Sarpong, Ph.D.