Details
| Original language | English |
|---|---|
| Pages (from-to) | 4946-4952 |
| Number of pages | 7 |
| Journal | Chemistry - a European journal |
| Volume | 18 |
| Issue number | 16 |
| Publication status | Published - 16 Apr 2012 |
Abstract
The improved synthesis of the antitumor compound (+)-tedanolide is described through an aldol coupling of bis-ketone 7. This modification shortens the synthetic steps in the endgame and provides rapid access to this biologically important natural product. Additionally, it serves as a probe in order to unravel the conformational effects that impede or enable its successful synthesis. Having this way access to des-epoxy-tedanolide, its biological characterization surprisingly unravelled the mode of action to resemble candidaspongiolide rather than deoxytedanolide.
Keywords
- aldol, antitumor agents, natural products, tedanolide, vinylogous aldol
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Organic Chemistry
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In: Chemistry - a European journal, Vol. 18, No. 16, 16.04.2012, p. 4946-4952.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - An improved route to (+)-tedanolide and analysis of its subtle effects controlling conformation and biological behaviour
AU - Diaz, Nina
AU - Zhu, Mingzhao
AU - Ehrlich, Gunnar
AU - Eggert, Ulrike
AU - Muthukumar, Yazh
AU - Sasse, Florenz
AU - Kalesse, Markus
PY - 2012/4/16
Y1 - 2012/4/16
N2 - The improved synthesis of the antitumor compound (+)-tedanolide is described through an aldol coupling of bis-ketone 7. This modification shortens the synthetic steps in the endgame and provides rapid access to this biologically important natural product. Additionally, it serves as a probe in order to unravel the conformational effects that impede or enable its successful synthesis. Having this way access to des-epoxy-tedanolide, its biological characterization surprisingly unravelled the mode of action to resemble candidaspongiolide rather than deoxytedanolide.
AB - The improved synthesis of the antitumor compound (+)-tedanolide is described through an aldol coupling of bis-ketone 7. This modification shortens the synthetic steps in the endgame and provides rapid access to this biologically important natural product. Additionally, it serves as a probe in order to unravel the conformational effects that impede or enable its successful synthesis. Having this way access to des-epoxy-tedanolide, its biological characterization surprisingly unravelled the mode of action to resemble candidaspongiolide rather than deoxytedanolide.
KW - aldol
KW - antitumor agents
KW - natural products
KW - tedanolide
KW - vinylogous aldol
UR - http://www.scopus.com/inward/record.url?scp=84859582894&partnerID=8YFLogxK
U2 - 10.1002/chem.201103038
DO - 10.1002/chem.201103038
M3 - Article
C2 - 22392854
AN - SCOPUS:84859582894
VL - 18
SP - 4946
EP - 4952
JO - Chemistry - a European journal
JF - Chemistry - a European journal
SN - 0947-6539
IS - 16
ER -