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Synthesis of Highly Functionalised Enantiopure Bicyclo[3.2.1]- octane Systems from Carvone

Author(s): Antonio Abad | Consuelo Agulló | Ana C. Cuñat | Ignacio de Alfonso | Ismael Navarro | Noelia Vera

Journal: Molecules
ISSN 1420-3049

Volume: 9;
Issue: 5;
Start page: 287;
Date: 2004;
Original page

Keywords: Carvone | Diels-Alder reaction | cyclopropane cleavage | 5-vinyl-1 | 3- cyclohexadiene | samarium diiodide | bicyclo[3.2.1]octane | tricyclo[]octane

The commercially available monoterpene carvone has been efficiently convertedinto the tricyclo[]octane and bicyclo[3.2.1]octane systems characteristic of somebiologically active compounds. The sequence used for this transformation involves as keyfeatures an intramolecular Diels-Alder reaction of a 5-vinyl-1,3-cyclohexadiene and acyclopropane ring opening.
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