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Molecules. 2004 Apr 30;9(5):287-99.

Synthesis of highly functionalised enantiopure bicyclo[3.2.1]- octane systems from carvone.

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  • 1Departamento de Química Orgánica, Facultad de Ciencias Químicas, Dr. Moliner, 50, 46100-Burjasot, (Valencia), Spain. antonio.abad@uv.es

Abstract

The commercially available monoterpene carvone has been efficiently converted into the tricyclo[3.2.1.0(2.7)]octane and bicyclo[3.2.1]octane systems characteristic of some biologically active compounds. The sequence used for this transformation involves as key features an intramolecular Diels-Alder reaction of a 5-vinyl-1,3-cyclohexadiene and a cyclopropane ring opening.

PMID:
18007432
[PubMed - indexed for MEDLINE]
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