A new enantiospecific route to sesquiterpenes of the calamenene family is described. The synthetic pathway starts from easily available 3-oxygenated-p-menthane monoterpenes and affords the title compounds by a homologation-benzannulation sequence. The trans and cis isomers of the natural compounds calamenene and 8-hydroxycalamenene were obtained in enantiopure form starting from (-)-menthone and (+)-isomenthone, respectively.
Aromatic annulation on the p-menthane monoterpenes: enantiospecific synthesis of the trans and cis isomers of calamenene and 8-hydroxycalamenene
Serra S;Fuganti C
2005
Abstract
A new enantiospecific route to sesquiterpenes of the calamenene family is described. The synthetic pathway starts from easily available 3-oxygenated-p-menthane monoterpenes and affords the title compounds by a homologation-benzannulation sequence. The trans and cis isomers of the natural compounds calamenene and 8-hydroxycalamenene were obtained in enantiopure form starting from (-)-menthone and (+)-isomenthone, respectively.File in questo prodotto:
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Descrizione: Tetrahedron Lett. 2005, 46, 4769-4772
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