Details
| Originalsprache | Englisch |
|---|---|
| Seiten (von - bis) | 6038-6041 |
| Seitenumfang | 4 |
| Fachzeitschrift | Organic letters |
| Jahrgang | 13 |
| Ausgabenummer | 22 |
| Publikationsstatus | Veröffentlicht - 18 Nov. 2011 |
Abstract
The challenging synthesis of a quaternary center within the highly oxygenated setting of tedanolide C can be performed via a Kiyooka aldol reaction. Here, the diastereomeric analog of tedanolide C with the configurations between C10 and C20 opposite compared to the proposed structure was chosen as the synthetic target. The tetra-substituted silyl ketene acetal provides the southern hemisphere of tedanolide C in useful selectivities, and the absolute configuration of the newly generated quaternary center was determined by NOE experiments of the corresponding acetonide.
ASJC Scopus Sachgebiete
- Biochemie, Genetik und Molekularbiologie (insg.)
- Biochemie
- Chemie (insg.)
- Physikalische und Theoretische Chemie
- Chemie (insg.)
- Organische Chemie
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in: Organic letters, Jahrgang 13, Nr. 22, 18.11.2011, S. 6038-6041.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review
}
TY - JOUR
T1 - A kiyooka aldol approach for the synthesis of the C(14)-C(23) segment of the diastereomeric analog of tedanolide C
AU - Bülow, Leila
AU - Naini, Arun
AU - Fohrer, Jörg
AU - Kalesse, Markus
PY - 2011/11/18
Y1 - 2011/11/18
N2 - The challenging synthesis of a quaternary center within the highly oxygenated setting of tedanolide C can be performed via a Kiyooka aldol reaction. Here, the diastereomeric analog of tedanolide C with the configurations between C10 and C20 opposite compared to the proposed structure was chosen as the synthetic target. The tetra-substituted silyl ketene acetal provides the southern hemisphere of tedanolide C in useful selectivities, and the absolute configuration of the newly generated quaternary center was determined by NOE experiments of the corresponding acetonide.
AB - The challenging synthesis of a quaternary center within the highly oxygenated setting of tedanolide C can be performed via a Kiyooka aldol reaction. Here, the diastereomeric analog of tedanolide C with the configurations between C10 and C20 opposite compared to the proposed structure was chosen as the synthetic target. The tetra-substituted silyl ketene acetal provides the southern hemisphere of tedanolide C in useful selectivities, and the absolute configuration of the newly generated quaternary center was determined by NOE experiments of the corresponding acetonide.
UR - http://www.scopus.com/inward/record.url?scp=80955129964&partnerID=8YFLogxK
U2 - 10.1021/ol202515x
DO - 10.1021/ol202515x
M3 - Article
C2 - 22026452
AN - SCOPUS:80955129964
VL - 13
SP - 6038
EP - 6041
JO - Organic letters
JF - Organic letters
SN - 1523-7060
IS - 22
ER -