Rapid construction of the ABD tricyclic skeleton in meliacarpinin B from carvone enabled by an INOC strategy

Abstract

A highly diastereoselective synthesis of the ABD skeleton of meliacarpinin B is presented. The construction of the key trans-decalin unit features an intramolecular nitrile oxide-alkene cycloaddtion (INOC) reaction on a readily available carvone derivative. This strategy enabled prepration of the tricyclic core bearing 6 contiguous stereogenic centres in 14 straightforward linear steps from R-carvone.