Synthesis of Desepoxy-Tedanolide C

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Original languageEnglish
Pages (from-to)7085-7089
Number of pages5
JournalChemistry - a European journal
Volume27
Issue number24
Early online date9 Apr 2021
Publication statusPublished - 26 Apr 2021

Abstract

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.

Keywords

    Kiyooka aldol, polyketides, structure elucidation, tedanolie C, tertiary alcohol

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Cite this

Synthesis of Desepoxy-Tedanolide C. / Lücke, Daniel; Kalesse, Markus.
In: Chemistry - a European journal, Vol. 27, No. 24, 26.04.2021, p. 7085-7089.

Research output: Contribution to journalArticleResearchpeer review

Lücke D, Kalesse M. Synthesis of Desepoxy-Tedanolide C. Chemistry - a European journal. 2021 Apr 26;27(24):7085-7089. Epub 2021 Apr 9. doi: 10.1002/chem.202100553
Lücke, Daniel ; Kalesse, Markus. / Synthesis of Desepoxy-Tedanolide C. In: Chemistry - a European journal. 2021 ; Vol. 27, No. 24. pp. 7085-7089.
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