Naturstoffe als reichhaltige Quelle für Pharmazeutika und innovative Chemische Transformationen: Plattformentwicklung für die Generierung von neuen antiviralen Verbindungen, fresshemmenden Terpenoiden und neuartige Methodologie für die chemische Synthese

• Antragsteller: Professor Dr. Thomas Magauer
• Fachliche Zuordnung: Organische Molekülchemie - Synthese, Charakterisierung
• Förderung: Förderung von 2013 bis 2018
• Projektkennung: Deutsche Forschungsgemeinschaft (DFG) - Projektnummer 244325724

• Erstellungsjahr: 2018

Zusammenfassung der Projektergebnisse

Natural products have inspired us throughout this project: We developed the first and only modular synthesis of antibiotic meroterpenoids, realized a highly convergent route to more than 15 antifeedant leucosceptroids and established the first one-pot b-halogenation of enones. It was exciting to see that several tetracyclic meroterpenoids possess highbiological activity against MRSA strains. These results are a good starting point for future structure-activity relationship (SAR) studies with the ultimate goal to develop new antibiotics against gram-negative bacteria (the Holy Grail in antibiotic research). With this project, we also want to spark further interest in the community to focus on antibiotic research. The importance of the obtained results was also recognized by the Austrian Press Agency (APA) and several newspapers. The fact that we could shine light on the biosynthesis of the leucosceptroids inspired us to investigate the related and equally fascinating natural product dictyoxetane. In the case of the latter we investigated a bioinspired synthesis that ultimately led to a revised biosynthesis. In addition, our studies revealed that dictyoxetane is unable to inhibit bacteria and cancer cells.

Projektbezogene Publikationen (Auswahl)

• A Modular Synthesis of Tetracyclic Meroterpenoid Antibiotics. Nat. Commun., 2017, 8, 2083
  R. Wildermuth, K. Speck, F.- L. Haut, P. Mayer, B. Karge, M. Brönstrup, T. Magauer
  
• Bioinspired Total Syntheses of Terpenoids. Org. Biomol. Chem. 2017, 15, 12–16
  C. L. Hugelshofer, T. Magauer
  
• De Novo Synthesis of Benzannelated Heterocycles.Chem. Eur. J., 2017
  J. Feierfeil, T. Magauer
  
• Development of a β-C–H Bromination Approach Towards the Synthesis of Jerantinine. J. Org. Chem., 2017, 82, 7410–7419
  E. T. Huber, T. Unzner, C. Gerlinger, T. Magauer
  
• Dyotropic Rearrangements in Natural Product Synthesis and Biosynthesis. Nat. Prod. Rep., 2017, 34, 228–234
  C. L. Hugelshofer, T. Magauer