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Molecules 2004, 9(5), 287-299; doi:10.3390/90500287
Article

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

* , , * , ,  and
Departamento de Química Orgánica. Facultad de Ciencias Químicas. Dr. Moliner, 50, 46100-Burjasot, (Valencia), Spain
* Authors to whom correspondence should be addressed.
Received: 2 February 2004 / Accepted: 8 March 2004 / Published: 30 April 2004
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Abstract

The commercially available monoterpene carvone has been efficiently convertedinto the tricyclo[3.2.1.02.7]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.
Keywords: Carvone; Diels-Alder reaction; cyclopropane cleavage; 5-vinyl-1; 3- cyclohexadiene; samarium diiodide; bicyclo[3.2.1]octane; tricyclo[3.2.1.02.7]octane Carvone; Diels-Alder reaction; cyclopropane cleavage; 5-vinyl-1; 3- cyclohexadiene; samarium diiodide; bicyclo[3.2.1]octane; tricyclo[3.2.1.02.7]octane
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Abad, A.; Agulló, C.; Cuñat, A.C.; De Alfonso, I.; Navarro, I.; Vera, N. Synthesis of Highly Functionalised Enantiopure Bicyclo[3.2.1]- octane Systems from Carvone. Molecules 2004, 9, 287-299.

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