Cubane was first theorized to exist by Thorpe and Beesley 1 over 100 years ago and consists of eight nominally sp -hybridized carbon atoms bonded together to produce a highly strained cubic structure. Cubane is not only interesting because of its peculiarity as a hydrocarbon Platonic solid, but it is also a useful bioisostere for the benzene ring due to its similar size and shape (Scheme 1A). Therefore the 1,4-substitution pattern of a cubane molecule could replace a para-substituted phenyl ring in a molecule and potentially offer improved properties including a departure from "flat-land". Furthermore, there are other uses for cubane and its derivatives such as its ability to rearrange into cunenes, its utilization in explosives and its incorporation into polymers. The first successful synthesis of cubane was accomplished by Eaton and Cole 10 to give dimethyl cubane-1,4-dicarboxylate 1 in 8 steps with a 12% overall yield from cyclopentenone. Subsequent routes by and Tsanaktsidis 12 allowed for cyclopentanone to be used as starting material at comparable synthetic efficiency and overall yield. Further optimizations of Tsanaktsidis's route by Linclau and co-workers allowed for the synthesis of decagram quantities of 1 in overall yields of between 33-40%. Despite extensive work, current synthetic routes to 1 rely upon the synthesis of key building block dibromo-dione 2 from cyclopentanone in 5 steps (Scheme 1B).