Syntheses and Structure Elucidation of Meridamycin

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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.