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

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