Details
| Original language | English |
|---|---|
| Pages (from-to) | 7085-7089 |
| Number of pages | 5 |
| Journal | Chemistry - a European journal |
| Volume | 27 |
| Issue number | 24 |
| Early online date | 9 Apr 2021 |
| Publication status | Published - 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
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Organic Chemistry
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In: Chemistry - a European journal, Vol. 27, No. 24, 26.04.2021, p. 7085-7089.
Research output: Contribution to journal › Article › Research › 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 -