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 (+/-)-herbertene.
Bernard
Angela M
AM
Dipartimento di Scienze Chimiche, Università di Cagliari, Complesso Universitario di Monserrato, S.S 554 Bivio per Sestu, I 09042 Monserrato (Cagliari), Italy.
Frongia
Angelo
A
Secci
Francesco
F
Piras
Pier P
PP
D000143:Acids / Q000737:chemistry*; D002384:Catalysis; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry
D000143:Acids; D003517:Cyclopentanes; D012717:Sesquiterpenes; C518145:alpha-cuparenone; C518146:herbertene; C007201:cyclopentanone