Bacterial drug resistance is a major concern to the World Health Organisation and the future of human health. Increasing resistance is consistently being observed to all commonly used antibiotic agents, and more recently to the last-line antibiotic agents used when all other drugs fail. This is of major concern in all bacterial species, but it is of special concern in deadly and infectious bacteria such as Mycobacterium tuberculosis. This projected aimed at synthesising chemical agents which would act as probes investigating their antibiotic activity via a new mechanism of action previously unseen in current antibiotic agents in use today. Target compounds were derived from a structure mimicking that of a natural product, aurachin RE, which shows some antibiotic activity in a new mechanism of action. This mechanism of action is based upon the inhibition of the bacterial production of menaquinone, as menaquinone is used to shuttle electrons within its electron transport chain. This structure shows inhibitory action at a particular enzyme step, MenA, in the biosynthetic pathway of menaquinone. These target compounds were derived from retrosynthetic analysis, whereby the final target structures were based on preserving the key structure activity relationships present in aurachin RE. These target compounds will serve as probes in future research to further the understanding of the structure activity relationships with respect to MenA inhibition to provide the groundwork for further generations of compounds with increased inhibition and bactericidal activity compared to that of aurachin RE.