A concise synthetic approach to construct the [6,8,6]-tricyclic core of taxezopidines A and B, which contains a synthetically challenging bridged bicyclo[5.3.1]undecane ring system bearing most of the desired functionalized groups and stereocenters, has been established. This approach features a diastereoselective type II intramolecular Diels-Alder furan reaction. The stereochemistry of the acetoxy group at the allylic position of the dienophile alkene group, such as in 6a, was found to be critical for achieving the desired highly diastereoselective outcome.