Noradamantane (tricyclo[3.3.1.03,7]nonane) is a tricyclic hydrocarbon compound with a molecular formula of C9H14 and C2v symmetry. As its name suggests, it is a methylene-shortened analogue of adamantane, probably the most frequently used cage compound in organic chemistry. This review focuses on the synthesis of still rather rare noradamantane derivatives that, due to the geometry of the parent carbon framework, exhibit different properties to their adamantane congeners. Synthetic strategies towards noradamantane derivatives include construction of the tricyclic structure from monocyclic compounds, ring closures of bicyclic compounds, ring-contractions of adamantane derivatives, skeletal rearrangements of compounds with the same molecular formula and directed C–H functionalization reactions performed on the noradamantane framework.
