Date of Award
Master of Science
George W. Kabalka
Richard Pagni, Bin Zhao
This dissertation summarizes the development of novel synthetic methods involving organometallic reagents and their application in the total synthesis of the natural product eupomatilone 2. These newly discovered reactions include the palladium-catalyzed cross-coupling of allyl acetates with organosiloxanes and the diastereoselective synthesis of cis- and trans-a-methylene-y-lactones utilizing Baylis-Hillman adducts as precursors. Another important aspect of the research is the application of some of the methods in total synthesis of eupomatilone 2.
The new synthetic methodologies involving organometallic reagents developed in this dissertation are important transformations in modern organic synthesis. Mild reaction conditions, tolerance of various organic functional groups, and high selectivity are advantages of these methodologies. The ability to recycle the catalytic system in some cases is another attractive feature for PEG-involved methods. The short and efficient strategy for the synthesis of eupomatilone 2 could serve as a catalyst for research in this area.
Chen, Chunlan, "Development of Novel Synthetic Methods Utilizing Organometallic Reagents and Total Synthesis of Eupomatilone 2. " Master's Thesis, University of Tennessee, 2006.