10.4225/03/58b4eb91c1654 Cao, Jia Jia Cao A stereoselective isoprenoid synthetic methodology and the preparation of a mycobacterial antigen Monash University 2017 Chiral isoprenoid moiety Fragrances monash:110934 thesis(doctorate) 1959.1/813840 (R)-2-Methylheptyl isonicotinate Mycobacterial antigen ethesis-20130301-12065 Open access Asymmetric synthesis 2013 Sex pheromone 2017-02-28 03:16:32 Thesis https://bridges.monash.edu/articles/thesis/A_stereoselective_isoprenoid_synthetic_methodology_and_the_preparation_of_a_mycobacterial_antigen/4700980 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.