Stereoselective Synthesis of a Bicyclic Norsesquiterpene Backbone - A Possible Route to Nardosinane Derivatives

We have developed an efficient diastereoselective synthetic route towards a nardosinane sesquiterpene scaffold. The strategy used a key bicyclic diene intermediate 11a, and allowed access to valuable polyoxygenated sesquiterpenes 21 and 22, which may be regarded as analogues of the natural sesquiterpenes laevinol B and fulvol acetate, respectively.