A Nucleophile-Catalyzed Cycloisomerization Permits a Concise Synthesis of (+)-Harziphilone

Substantial structural transformations of much use in complex chemical synthesis can be achieved by channeling the reactivity of highly unsaturated molecules. This report describes the direct conversion of an acyclic polyunsaturated diketone to the HIV-1 Rev/Rev-responsive element inhibitor harziphi...

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Bibliographic Details
Published in:Proceedings of the National Academy of Sciences - PNAS 2004-08, Vol.101 (33), p.12064-12066
Main Authors: Stark, Lucy M., Pekari, Klaus, Sorensen, Erik J., Nicolaou, Kyriacos C.
Format: Article
Language:English
Subjects:
Alcohols
Aldehydes
Anti-HIV Agents - chemical synthesis
Anti-HIV Agents - chemistry
Benzopyrans - chemical synthesis
Benzopyrans - chemistry
Carbon
Catalysis
Catalysts
Chemical reactions
Chemical synthesis
Chemistry
Chemistry, Organic - methods
Diones
HIV 1
Human immunodeficiency virus 1
Molecular Structure
Molecules
Natural Product Synthesis Special Feature
Nucleophiles
Physical Sciences
Piperazines
Reactivity
Room temperature
Stereoisomerism
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Summary:Substantial structural transformations of much use in complex chemical synthesis can be achieved by channeling the reactivity of highly unsaturated molecules. This report describes the direct conversion of an acyclic polyunsaturated diketone to the HIV-1 Rev/Rev-responsive element inhibitor harziphilone under mild reaction conditions.
ISSN:0027-8424
1091-6490
DOI:10.1073/pnas.0402563101