Syntheses and Structure Elucidation of Meridamycin

• Applicant: Professor Dr. Markus Kalesse
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: since 2017
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 328899403

The aim of this project is still the total synthesis of meridamycin. With the envisioned synthesis, the synthetic access to this natural product and the validity of our Hidden-Markov-Modell for the prediction of configurations at polyketides should be validated. For the rapid assessment of the configurations we plan to synthesize the open-chain analog of meridamycin, meridamycin D. Additionally, we plan to investigate the scope and limitations of our recently developed alternative to the Nozaki-Hiyama-Kishi reaction, our 1,2-metallate rearrangement using vinyl boronates. This investigation will be performed using a variety of different polyketide fragments in order to investigate their selectivities in the absence of sparteine. This can ultimately lead to a new and highly valuable method for the total synthesis of natural products. Both, the Hidden-Markov-Modell prediction of chirality as well as the 1,2-metallate rearrangement will funnel into the total synthesis of meridamycin and help to circumvent the poor yields observed in pivotal aldo steps of both hemispheres.

• DFG Programme: Research Grants