Total Synthesis and Biological Evaluation of (−)-9-Deoxy-englerin A

An effective total synthesis of (−)-9-deoxy-englerin (4), an analogue of the natural guaiane sesquiterpene englerin A (1), has been achieved. The synthesis features a transannular epoxide opening to construct the 5,7-fused ring system followed by transannular ether formation with mercury(II) trifluo...

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Bibliographic Details
Published in:Organic letters 2011-04, Vol.13 (8), p.2090-2093
Main Authors: Ushakov, Dmitry B, Navickas, Vaidotas, Ströbele, Markus, Maichle-Mössmer, Cäcilia, Sasse, Florenz, Maier, Martin E
Format: Article
Language:English
Subjects:
Alkylation
Cell Line
Cell Proliferation - drug effects
Cyclization
Humans
Models, Molecular
Molecular Structure
Sesquiterpenes, Guaiane - chemical synthesis
Sesquiterpenes, Guaiane - pharmacology
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Summary:An effective total synthesis of (−)-9-deoxy-englerin (4), an analogue of the natural guaiane sesquiterpene englerin A (1), has been achieved. The synthesis features a transannular epoxide opening to construct the 5,7-fused ring system followed by transannular ether formation with mercury(II) trifluoroacetate.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol200499t