This PhD thesis describes the laboratory scale preparation of a number of optically active, cyclopropane containing building blocks that are derived from simple, readily available starting materials. The methodologies employed during the completion of these studies may be readily divided into two discrete groups: Firstly, the chemical resolution of racemic starting materials via both reagent and enzymatically mediated routes. And secondly, the induced stereoselective cyclopropanation of optically active starting materials drawn directly from the "chiral pool". The racem1c cyclopropane containing carboxylic acids 2,2-dibromo-1-methylcyclopropanecarboxylic acid (i), and 2,2-dibromocyclopropanecarboxylic acid (ii) were readily resolved in moderate yields using the commercially available optically active ammes, (+)-dehydroabietylan1ine a nd (+) or (-)-(a)-methyl benzylamine respectively. Furthermore, the resolved carboxylic acids (+) and (-)-(ii) have successfully been employed in the development of a versatile synthetic route that enables the stereocontrolled stepwise construction of polycyclopropane containing arrays such as those found in the natural products FR-900848 and U-106305, examples prepared include (iii -vi). The stereocontrolled cyclopropanation of the unsaturated sugar methyl-4,6-O-benzylidene-a-D-erythro-hex-2-enopyranoside has allowed the moderately large-scale preparation of the polyfunctionalised chiral building block, ((1R,3S)-2,2-dichloro-3-[1,3)dithian-2-yl-cyclopropyl)-propane-l ,2,3-triol, a molecule that shows considerable potential fo r application in synthesis.