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Originalpublikation
Lücke, D.; Kalesse, M.: Synthesis of Desepoxy-Tedanolide C. In: Chemistry – A European Journal 27 (2021), Nr. 24, S. 7085-7089. DOI: https://doi.org/10.1002/chem.202100553
The synthesis of desepoxy-tedanolide C was accomplished and provided experimental evidence on the configuration of tedanolide C. The reported chemical shifts and coupling constants point to a configuration different from the published structure and analogous to the structures of the other members of this family of natural products. The key step is a Kiyooka aldol protocol for the stereoselective synthesis of the tertiary alcohol flanked by three additional oxygenated carbon atoms. Furthermore, two additional aldol reactions and a Julia–Kocienski olefination were used to assemble the carbon framework.