Details
| Originalsprache | Englisch |
|---|---|
| Seiten (von - bis) | 7085-7089 |
| Seitenumfang | 5 |
| Fachzeitschrift | Chemistry - a European journal |
| Jahrgang | 27 |
| Ausgabenummer | 24 |
| Frühes Online-Datum | 9 Apr. 2021 |
| Publikationsstatus | Veröffentlicht - 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.
ASJC Scopus Sachgebiete
- Chemische Verfahrenstechnik (insg.)
- Katalyse
- Chemie (insg.)
- Organische Chemie
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in: Chemistry - a European journal, Jahrgang 27, Nr. 24, 26.04.2021, S. 7085-7089.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review
}
TY - JOUR
T1 - Synthesis of Desepoxy-Tedanolide C
AU - Lücke, Daniel
AU - Kalesse, Markus
PY - 2021/4/26
Y1 - 2021/4/26
N2 - 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.
AB - 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.
KW - Kiyooka aldol
KW - polyketides
KW - structure elucidation
KW - tedanolie C
KW - tertiary alcohol
UR - http://www.scopus.com/inward/record.url?scp=85104077719&partnerID=8YFLogxK
U2 - 10.1002/chem.202100553
DO - 10.1002/chem.202100553
M3 - Article
AN - SCOPUS:85104077719
VL - 27
SP - 7085
EP - 7089
JO - Chemistry - a European journal
JF - Chemistry - a European journal
SN - 0947-6539
IS - 24
ER -