The conversion of podocarpic acid to hexahydrophenalene derivatives: an approach to the synthesis of edulone A

Abstract

To test the feasibility of a biogenetically inspired synthesis of edulone A 1, podocarpic acid 3a has been transformed into a substituted hexahydrophenalene 16b. The critical steps involve introduction of a double bond into the A ring, cleavage by ozone, and, after suitable manipulation, an epoxy-arene cyclization. A second product from this cyclization is an octahydrophenaleno[1,9-bc]furan 17.