2,2-dimethyl cyclopentanones by acid catalyzed ring expansion of isopropenylcyclobutanols. A short synthesis of (+/-)-alpha-cuparenone and (+/-)-herbertene

2,2-dimethyl cyclopentanones are readily prepared by acid catalyzed ring expansion of isopropenylcyclobutanols; the method allows ready access to the family of sesquiterpenes cuparanes and herbertanes, as demonstrated by the synthesis of (+/-)-alpha-cuparenone and the direct precursor of (+/-)-herbe...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2005-08 (30), p.3853-3855
Main Authors: Bernard, Angela M, Frongia, Angelo, Secci, Francesco, Piras, Pier P
Format: Article
Language:English
Subjects:
Acids - chemistry
Catalysis
Cyclopentanes - chemical synthesis
Cyclopentanes - chemistry
Methylation
Molecular Structure
Sesquiterpenes - chemical synthesis
Sesquiterpenes - chemistry
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Summary:2,2-dimethyl cyclopentanones are readily prepared by acid catalyzed ring expansion of isopropenylcyclobutanols; the method allows ready access to the family of sesquiterpenes cuparanes and herbertanes, as demonstrated by the synthesis of (+/-)-alpha-cuparenone and the direct precursor of (+/-)-herbertene.
ISSN:1359-7345
1364-548X
DOI:10.1039/b505707h