Development of the Synthesis of Desepoxy-Tedanolide C

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Original languageEnglish
Pages (from-to)2408–2430
Number of pages23
JournalJournal of Organic Chemistry
Volume89
Issue number4
Early online date25 Jan 2024
Publication statusPublished - 16 Feb 2024

Abstract

We are presenting the development of our route for the total synthesis of desepoxy-tedanolide C. Through the obtained analytical data, the proposed structure of tedanolide C is questioned and a different configuration for this natural product is proposed. Key steps of the synthesis are a Kiyooka aldol reaction that builds up the tertiary alcohol flanked by three oxygenated carbon atoms and two aldol reactions used for fragment couplings. A Julia-Kocienski olefination was used for installation of the side chain. Besides the successful synthesis, the development for the protecting group setup of the southwestern hemisphere is described in detail as well as another retrosynthetic attempt for building up the target molecule.

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Development of the Synthesis of Desepoxy-Tedanolide C. / Lücke, Daniel; Kalesse, Markus.
In: Journal of Organic Chemistry, Vol. 89, No. 4, 16.02.2024, p. 2408–2430.

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Lücke D, Kalesse M. Development of the Synthesis of Desepoxy-Tedanolide C. Journal of Organic Chemistry. 2024 Feb 16;89(4):2408–2430. Epub 2024 Jan 25. doi: 10.1021/acs.joc.3c02437
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AU - Kalesse, Markus

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