Details
| Original language | English |
|---|---|
| Pages (from-to) | 6038-6041 |
| Number of pages | 4 |
| Journal | Organic letters |
| Volume | 13 |
| Issue number | 22 |
| Publication status | Published - 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 subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: Organic letters, Vol. 13, No. 22, 18.11.2011, p. 6038-6041.
Research output: Contribution to journal › Article › Research › 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 -