Comprehensive Synthesis of a Group of Optically Active Caged Hydrocarbon Molecules—Cubane Scaffold Editing—

Small polyhedral hydrocarbons represented by cubane have attracted attention as potential molecular scaffolds for pharmaceuticals as benzene bioisostere. Cubane is also expected to be used as a chiral scaffold, but due to its high symmetry, it is necessary to introduce chirality by sequential site-selective introduction of substituents. Furthermore, polyhedral desymmetrized isomers of cubane, such as cuneane and semibullvalene, and extended cage compounds, such as bishomocubane and homocuneane, exhibit chirality and are also expected to be used as new chiral scaffolds. In this concept, we would like to explain our synthetic routes, particularly focusing on the decoration and editing of the cubane skeleton.