Current Research Interests

The majority of the research personnel in my group are currently engaged in three general fields of interest: the development of new synthetic methods, the total synthesis of biologically active natural products, and medicinal chemistry. We are pursuing the total synthesis of several promising antitumor agents, e.g., tedanolide and 13-deoxytedanolide, dichlorolissoclimide, haterumaimide E, the auripyrones, the cucurbitacins, rugulosone, gymnostatin G, and oridonin. The use of epoxide rearrangements in synthesis, e.g., the non-aldol aldol process, and others, is under investigation as well, especially for the synthesis of new antibiotics of the erythromycin class and the rifamycins. We are also studying the use of various reactions (e.g., Diels-Alder reactions and [3,3] rearrangements) for the synthesis of biologically active molecules, e. g., the immunosuppressive agent brasilicardin A; the antibiotic fusidic acid; the antibacterial agent mycosporulone; and multiple drug resistance reversing agents such as welwitindolinone C. In particular, we are developing the mixed Lewis acid system, 5:1 AlBr3:AlMe3, in a variety of reactions, e.g., cycloadditions, nucleophilic additions, etc. We are developing new processes for the efficient synthesis of polyhydroxylated steroids, e.g., the cardioactive agent ouabain and the anticancer agent rhodexin A. We have several collaborative programs in medicinal chemistry, e.g.: a) the preparation and testing of novel small molecule androgen receptor antagonists which are very active at inhibiting the growth of castration-resistant prostate cancer; b) the preparation of various naturally occurring oxidation products of arachidonic acids, epoxy isoprostanes such as PEIPC (which are involved in the onset of atherosclerosis); c) the development of a new method of delivering antibacterial agents to resistant bacterial strains; d) the preparation and testing of new selective binders for the estrogen receptor as potential anti-breast cancer agents; e) the preparation and testing of small molecules which differentiate stem cells into osteoblasts for bone growth; f) the design and preparation of small molecule inhibitors of the growth of several enveloped viruses, e.g., HIV, Hepatitis C; g) the design and preparation of small molecule inhibitors of mycolyl transferase as anti-TB agents; h) the design and synthesis of novel small molecule radiomitigators; and i) the preparation of molecules that bind to the Sortase-A binding pocket to determine the structure of this important medicinal target and as potential antibacterial agents. We are also investigating the development of new reaction for synthesis, e.g., the non-aldol aldol process, the bridged Robinson annulation, and the mixed Lewis acid Diels-Alder process.

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