|Title:||Studies Toward the Total Synthesis of Hinckdentine A using Under Utilised Reactions and Functional Groups|
|Publisher:||University of Sydney.|
Faculty of Science.
School of Chemistry.
|Abstract:||Many useful organic transformations remain underutilised because they have not been thoroughly investigated and understood. We have sought to expand the utility of neglected reactions and functional groups by investigating their mechanism and examining their scope. We planned to demonstrate utility of these transformations by incorporating them as key steps in the total synthesis of the natural product hinckdentine A. We developed a rational and consistent theory for mechanism of on-water catalysis. This new theory has allowed us to identify previously unrecognised examples of this phenomenon. The traditionally difficult conjugate addition of anilines was found to be facile under on-water conditions and this reaction was further improved through the incorporation of N-acylpyrroles. N-Acylpyrroles were also found to facilitate the Stetter reaction and expand the scope of subsequent transformations. The understanding gained from these studies allowed us to undertake studies toward the total synthesis of hinckdentine A, by an innovative route which included the aforementioned reactions as integral transformations.|
|Type of Work:||PhD Doctorate|
|Type of Publication:||Doctor of Philosophy Ph.D.|
|Appears in Collections:||Sydney Digital Theses (Open Access)|
|phippen_cbw_thesis.pdf||PhD Thesis||9.39 MB||Adobe PDF|