A stereoselective isoprenoid synthetic methodology and the preparation of a mycobacterial antigen

Abstract

This thesis describes two separate research projects. The first one focused on the development of a new asymmetric synthetic methodology to construct isoprenoid moieties, which are present in a range of important bioactive natural products. Then the developed methodology was applied to the synthesis of several selected natural products, including a sex pheromone, fragrances, the side chain of zaragozic acid C, an intermediate of tuberculostearic acid, and the side chain of vitamin E. A purported natural product, with antibacterial and antifungal activities, (R)-2-methylheptyl isonicotinate, was also prepared. The second project focused on the preparation of a mycobacterial antigen, BbGLIIc, for evaluation of its immunological response.