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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
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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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