Enantioselective Synthesis of the Complex Rocaglate (-)-Silvestrol

Enantioselective Synthesis of the Complex Rocaglate (-)-Silvestrol

The total synthesis of the natural product (−)‐silvestrol (1) has been accomplished and features enantioselective [3+2] photocycloaddition of a substituted 3‐hydroxyflavone and methyl cinnamate promoted by a chiral Brønsted acid. Initial biological studies indicate a 5–10‐fold greater activity of si...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2007-01, Vol.46 (41), p.7831-7834
Hauptverfasser: Gerard, Baudouin, Cencic, Regina, Pelletier, Jerry, Porco, John A. Jr
Format: Artikel
Sprache:eng
Schlagworte:
Animals
antitumor agents
Benzofurans - chemistry
cycloaddition
Molecular Structure
natural products
photochemistry
Rabbits
Reticulocytes - drug effects
Stereoisomerism
total synthesis
Triterpenes - chemical synthesis
Triterpenes - chemistry
Triterpenes - pharmacology
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Beschreibung
Zusammenfassung:The total synthesis of the natural product (−)‐silvestrol (1) has been accomplished and features enantioselective [3+2] photocycloaddition of a substituted 3‐hydroxyflavone and methyl cinnamate promoted by a chiral Brønsted acid. Initial biological studies indicate a 5–10‐fold greater activity of silvestrol as an inhibitor of protein synthesis in HeLa cells than its 1′′′′ diastereomer.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200702707