Synthesis of Highly Functionalised Enantiopure Bicyclo3.2.1- octane Systems from Carvone

摘要

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.