Total Synthesis and Antibacterial Activity of Dysidavarone A

A concise total synthesis of dysidavarone A possessing the new “dysidavarane” carbon skeleton has been accomplished by a convergent strategy, involving a stereoselective reductive alkylation of a Wieland-Miescher type ketone under Birch conditions and an advantageous intramolecular palladium-catalyz...

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Bibliographic Details
Published in:Organic letters 2013-02, Vol.15 (4), p.964-967
Main Authors: Schmalzbauer, Björn, Herrmann, Jennifer, Müller, Rolf, Menche, Dirk
Format: Article
Language:English
Subjects:
Alkylation
Animals
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - pharmacology
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Catalysis
Dysidea - chemistry
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Palladium - chemistry
Quinones - chemical synthesis
Quinones - chemistry
Quinones - pharmacology
Sesquiterpenes - chemical synthesis
Sesquiterpenes - chemistry
Sesquiterpenes - pharmacology
Spiro Compounds - chemistry
Stereoisomerism
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Summary:A concise total synthesis of dysidavarone A possessing the new “dysidavarane” carbon skeleton has been accomplished by a convergent strategy, involving a stereoselective reductive alkylation of a Wieland-Miescher type ketone under Birch conditions and an advantageous intramolecular palladium-catalyzed α-arylation of a sterically hindered ketone. Dysidavarone A showed potent antimicrobial and antiproliferative activities based on characteristic morphological changes of treated cells.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol400156u