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I. Synthetic Studies towards NF00659B1 II. Design, Synthesis, and Characterization of Manassantin Analogues

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Thursday, July 09, 2015
1:00 pm - 4:00 pm
Do Yeon Kwon, Ph.D. candidate
Ph.D. Dissertation Defense

Despite natural products play a crucial role in drug discovery and chemical biology, these compounds are often available in limited quantities. Therefore, there is a need for efficient methods that allow access to the natural products as well as analogues for the evaluation of biological activity, investigation of structure activity relationships, and generation of more improved bioactive molecules. This dissertation consists of two parts focused on synthetic studies towards biologically active natural products and their analogues.Part I: Since bioactive diterpenoid pyrones produced by microbes have limitless potential in pharmaceutical applications, a considerable effort has been devoted to the synthesis of diterpenoid pyrones and the identification of their structure-activity relationships. This chapter describes our synthetic studies towards the first total synthesis of NF00659B1, the 4,5-seco-tricyclic diterpene ¿-pyrone. Our synthetic efforts are focused on an efficient construction of the key intermediate oxepanol and installation of the ¿-pyrone moiety by Cu(I)-mediated intermolecular SN2¿ reaction. Using efficient synthetic methods, we have been investigating the unknown absolute and relative stereochemistry of NF00659s. In addition, these synthetic strategies will contribute to a more thorough elucidation of their bioactivities. Due to their bioactivities, NF00659s are expected to be promising new anticancer drugs.