TitleHydrogen bonding catalysis and redox neutral cascade reactions
NameVecchione, Matthew K. (Matthew Kyle) (author), Seidel, Daniel (chair), Williams, Lawrence (internal member), Hultzsch, Kai (internal member), Rutgers University, Graduate School - New Brunswick,
SubjectChemistry and Chemical Biology,
DescriptionMy thesis is divided into two parts; hydrogen bonding catalysis and redox neutral cascade reactions. Relating to hydrogen bonding catalysis, I was successful in performing an addition of isothiocyanato imides to α-ketoesters, with the ultimate goal of synthesizing beta-hydroxy-alpha-amino acids. The necessity of more conventional means to develop catalytic, enantioselective, and diastereoselective routes to these moieties can be seen in their presence in many natural products, including vancomycin. Redox neutral chemistry has gained strong popularity due to its advantageous qualities, including: its green, environmental-friendly characteristics, lack of using expensive or harmful oxidants and reductants, and ability to build up molecular complexity with limited number of steps. Under this branch of chemistry, I was able to develop an acid-assisted indole addition to ortho-aminoaldehydes leading to the synthesis of quinoline derivatives. These compounds, although not studied extensively, have been discovered to be potent sirtuin protein inhibitors and precursors to number of simple natural products, including cryptosanguinolentine. A further study evaluating secondary aminobenzaldehydes and indole shows that the synthesis of the antimalarial agent neocryptolepine could be easily achieved. This simple methodology also makes it possible to synthesize analogues of this important natural product.
NoteIncludes bibliographical references
Noteby Matthew K. Vecchione
CollectionGraduate School - New Brunswick Electronic Theses and Dissertations
Organization NameRutgers, The State University of New Jersey
RightsThe author owns the copyright to this work.