Event Information
I. Total Syntheses and Biological Studies of Largazole and Brasilibactin A
II. Stereoselective Synthesis of 2,6-Cis- and 2,6-Trans-Piperidines through an Organocatalytic Aza-Michael Reaction
- Abstract:
The focus of this dissertation contains three main projects which complement the studies towards the total syntheses of biologically active natural products as well as the development of stereoselective synthesis of 2,6-disubstituted piperidines. The first project introduced the first total synthesis of largazole, which is potent class I histone deacetylase inhibitor (HDACi). Through the structure-activity relationship (SAR) studies, pharmocophore and structural requirement for its HDAC inhibitory activity were determined. The second project involved the synthesis of cytotoxic mycobactin-like siderophore-brasilibactin A and its analogues, and also included the iron-binding studies of a new water-soluble analogue-Bbtan. The third project elucidated a convergent stereoselective synthesis of 2,6-cis- and 2,6-trans-piperidines through a reagent-controlled organocatalytic aza-Michael reaction promoted by the gem-disubstituent effect introduced by 1,3-dithiane. This synthetic method would be broadly applicable to the efficient synthesis of a diverse set of bioactive natural products containing 2,6-disubstituted piperidines.
Ph.D. Dissertation Defense Examination Seminar
Student Exams Seminar