A stereocontrolled total synthesis of (±)-zizaene

A stereocontrolled approach to the construction of the tricyclo[6.2.1.01,5]undecane ring system related to the sesquiterpene zizaene is delineated. Starting from an indanone, a bromophenol was prepared in a straightforward manner. An intramolecular anionic cyclisation then afforded a tricyclic dienone which was stereoselectively converted into a mesylate through various intermediates. Base induced rearrangement furnished a trans-fused ketone as the sole product which was converted into (±)-zizaene through Wittig olefination.