This thesis describes the synthetic studies performed utilizing tridentate Schiff base Cr(III) complex catalysts towards the total synthesis of ()-lasonolide A resulting in the completion of synthetic efforts towards the C17-C25 segment. Further summarization is also given on completion of the C7-C16 segment and an overview of future directions toward to the total synthesis of ()-lasonolide A. Both tetrahydropyrans C7-C11 and C19-C23 were to be constructed utilising an asymmetric hetero-Diels–Alder protocol involving Jacobsen’s hetero-Diels–Alder catalyst providing a means to generate a number of the desired stereocentres simultaneously in each ring system, followed by novel macrolide formation using ruthenium catalysts for metathesis olefination and Alder-ene chemistry. Jacobsen's hetero-Diels–Alder catalyst has also been utilised to generate C-disacharide linked precursors under diastereolective control in an effort to generate stereospecific 13 linked disaccharides.