Details
| Originalsprache | Englisch |
|---|---|
| Seiten (von - bis) | 2232-2247 |
| Seitenumfang | 16 |
| Fachzeitschrift | Chemistry - a European journal |
| Jahrgang | 14 |
| Ausgabenummer | 7 |
| Publikationsstatus | Veröffentlicht - 27 Feb. 2008 |
Abstract
Tedanolide, which was isolated by Schmitz in 1984 from the marine sponge Tedania ignis, is a highly cytotoxic macrolide leading to strong growth inhibition of P338 tumor cells in bioassays. A unique structural feature of the known tedanolides is the primary hydroxyl group incorporated in the macrolactone. This unusual motif for macrolactones originated from PKS biosynthesis might arise through lactonizations others than those derived by the thioesterase reaction. First experimental data that support this hypothesis and reflect the inherent preference of PKS-induced macrolactonization were obtained during this synthesis. The inherent preference for the formation of a 14-membered macrocyclization is discussed together with the pivotal steps in the synthesis.
ASJC Scopus Sachgebiete
- Chemische Verfahrenstechnik (insg.)
- Katalyse
- Chemie (insg.)
- Organische Chemie
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in: Chemistry - a European journal, Jahrgang 14, Nr. 7, 27.02.2008, S. 2232-2247.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review
}
TY - JOUR
T1 - The total synthesis of (+)-tedanolide - A macrocyclic polyketide from marine sponge tedania ignis
AU - Ehrlich, Gunnar
AU - Hassfeld, Jorma
AU - Eggert, Ulrike
AU - Kalesse, Markus
PY - 2008/2/27
Y1 - 2008/2/27
N2 - Tedanolide, which was isolated by Schmitz in 1984 from the marine sponge Tedania ignis, is a highly cytotoxic macrolide leading to strong growth inhibition of P338 tumor cells in bioassays. A unique structural feature of the known tedanolides is the primary hydroxyl group incorporated in the macrolactone. This unusual motif for macrolactones originated from PKS biosynthesis might arise through lactonizations others than those derived by the thioesterase reaction. First experimental data that support this hypothesis and reflect the inherent preference of PKS-induced macrolactonization were obtained during this synthesis. The inherent preference for the formation of a 14-membered macrocyclization is discussed together with the pivotal steps in the synthesis.
AB - Tedanolide, which was isolated by Schmitz in 1984 from the marine sponge Tedania ignis, is a highly cytotoxic macrolide leading to strong growth inhibition of P338 tumor cells in bioassays. A unique structural feature of the known tedanolides is the primary hydroxyl group incorporated in the macrolactone. This unusual motif for macrolactones originated from PKS biosynthesis might arise through lactonizations others than those derived by the thioesterase reaction. First experimental data that support this hypothesis and reflect the inherent preference of PKS-induced macrolactonization were obtained during this synthesis. The inherent preference for the formation of a 14-membered macrocyclization is discussed together with the pivotal steps in the synthesis.
KW - Aldol reactions
KW - Macrolactone
KW - Natural products
KW - Tedanolide
UR - http://www.scopus.com/inward/record.url?scp=52649114095&partnerID=8YFLogxK
U2 - 10.1002/chem.200701529
DO - 10.1002/chem.200701529
M3 - Article
C2 - 18165955
AN - SCOPUS:52649114095
VL - 14
SP - 2232
EP - 2247
JO - Chemistry - a European journal
JF - Chemistry - a European journal
SN - 0947-6539
IS - 7
ER -