Details
| Originalsprache | Englisch |
|---|---|
| Seiten (von - bis) | 2408–2430 |
| Seitenumfang | 23 |
| Fachzeitschrift | Journal of Organic Chemistry |
| Jahrgang | 89 |
| Ausgabenummer | 4 |
| Frühes Online-Datum | 25 Jan. 2024 |
| Publikationsstatus | Veröffentlicht - 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.
ASJC Scopus Sachgebiete
- Chemie (insg.)
- Organische Chemie
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in: Journal of Organic Chemistry, Jahrgang 89, Nr. 4, 16.02.2024, S. 2408–2430.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review
}
TY - JOUR
T1 - Development of the Synthesis of Desepoxy-Tedanolide C
AU - Lücke, Daniel
AU - Kalesse, Markus
N1 - Funding Information: This work was supported by the Deutsche Forschungsgemeinschaft (DFG) KA 913/25-1. We thank Dr. J. Fohrer, M. Rettstadt and D. Körtje for detailed NMR analysis and Dr. G. Dräger, A. Schulz and R. Reichel for mass spectra.
PY - 2024/2/16
Y1 - 2024/2/16
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85184762518&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.3c02437
DO - 10.1021/acs.joc.3c02437
M3 - Article
AN - SCOPUS:85184762518
VL - 89
SP - 2408
EP - 2430
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 4
ER -