Total synthesis of (±)-mycoepoxydiene, a novel fungal metabolite having an oxygen-bridged cyclooctadiene skeleton

The first total synthesis of (±)-mycoepoxydiene has been accomplished. A ring-closing olefin metathesis (RCM) approach was employed for the construction of the oxygen-bridged eight-membered bicyclic skeleton. The RCM product was converted to the target natural product featuring the oxidative rearrangement of a furfuryl alcohol introduced as the side chain and the stereoselective 1,2-reduction of a δ-keto-β,γ-unsaturated α-lactol intermediate.