Development of the Synthesis of Desepoxy-Tedanolide C

verfasst von

Daniel Lücke, Markus Kalesse

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.

Organisationseinheit(en)

Institut für Organische Chemie

Typ

Artikel

Journal

Journal of Organic Chemistry

Band

89

Seiten

2408–2430

Anzahl der Seiten

23

ISSN

0022-3263

Publikationsdatum

16.02.2024

Publikationsstatus

Veröffentlicht

Peer-reviewed

Ja

ASJC Scopus Sachgebiete

Organische Chemie

Elektronische Version(en)

https://doi.org/10.1021/acs.joc.3c02437 (Zugang: Offen)