Aromatic annulation on the p-menthane monoterpenes: enantiospecific synthesis of the trans and cis isomers of calamenene and 8-hydroxycalamenene |
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| Authors: | Stefano Serra Claudio Fuganti |
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| Affiliation: | C.N.R., Istituto di Chimica del Riconoscimento Molecolare, Sezione ‘Adolfo Quilico’ presso Dipartimento di Chimica, Materiali ed Ingegneria Chimica ‘Giulio Natta’ del Politecnico, Via Mancinelli 7, I-20133 Milano, Italy |
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| 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. |
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| Keywords: | Annulation Terpenes Calamenene Enantiospecific Tetralins |
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