Total Synthesis of the Callipeltoside Aglycon

Total Synthesis of the Callipeltoside Aglycon

Following macrolactonization, a Sonogashira coupling leads efficiently from 1 and 2 to the aglycon of the structurally unique cytotoxic macrolide callipeltoside A, isolated in tiny quantities from the lithistid sponge Callipelta sp. Key steps in the preparation of macrolide precursor 1 include a bor...

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Veröffentlicht in:Angewandte Chemie International Edition 2001-02, Vol.40 (3), p.603-607
Hauptverfasser: Paterson, Ian, Davies, Robert D. M., Marquez, Rodolfo
Format: Artikel
Sprache:eng
Schlagworte:
antitumor agents
boron
macrolides
natural products
total synthesis
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Beschreibung
Zusammenfassung:Following macrolactonization, a Sonogashira coupling leads efficiently from 1 and 2 to the aglycon of the structurally unique cytotoxic macrolide callipeltoside A, isolated in tiny quantities from the lithistid sponge Callipelta sp. Key steps in the preparation of macrolide precursor 1 include a boron‐mediated anti‐aldol coupling (A) in tandem with Yamamoto's vinylogous aldol reaction (B). TES=triethylsilyl.
ISSN:1433-7851
1521-3773
DOI:10.1002/1521-3773(20010202)40:3<603::AID-ANIE603>3.0.CO;2-O