Synthesis of Dimeric Terpenoyl Glycoside Side Chains from Cytotoxic Saponins

Synthesis of Dimeric Terpenoyl Glycoside Side Chains from Cytotoxic Saponins

A bottleneck in the synthesis of the model compound 1, which bears a dimeric terpenoyl glycoside side chain from cytotoxic saponins, was overcome by the stepwise construction of the terpene part by regioselective acylation of the sugar with a functionalized phosphonate followed by a Horner–Wadsworth...

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Veröffentlicht in:Angewandte Chemie International Edition 2004-08, Vol.43 (33), p.4353-4357
Hauptverfasser: Reicheneder, Sabine, Unverzagt, Carlo
Format: Artikel
Sprache:eng
Schlagworte:
Antineoplastic Agents - chemical synthesis
antitumor agents
carbohydrates
Dimerization
Glycosides - chemistry
natural products
olefination
saponins
Saponins - chemistry
Steroids - chemistry
Terpenes - chemistry
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Beschreibung
Zusammenfassung:A bottleneck in the synthesis of the model compound 1, which bears a dimeric terpenoyl glycoside side chain from cytotoxic saponins, was overcome by the stepwise construction of the terpene part by regioselective acylation of the sugar with a functionalized phosphonate followed by a Horner–Wadsworth–Emmons olefination.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200352895