Graduation Term
3-28-2023
Document Type
Thesis
Degree Name
Master of Science (MS)
Department
Department of Chemistry
Committee Chair
Shawn Hitchcock
Abstract
Since the emergence of AIDS in the early 1980s, strategies to mitigate the disease remain a high priority for medical professionals worldwide. While there is no broadly available cure or vaccine for HIV/AIDS at this time, early diagnosis and treatment can drastically reduce the severity of the infection. To this end, antiretroviral drugs are regularly employed to combat the virus and achieve HIV latency in infected patients. One such drug, Darunavir, has been used as a highly effective HIV protease inhibitor. Recently, a growing interest in derivatization of Darunavir to test for improved drug efficacy has prompted great efforts in the synthetic/medicinal chemistry community. However, synthetic constrictions of currently existing routes to Darunavir have made access to its analogues a difficult enterprise. The synthesis described herein is proposed to be an efficient, modular pathway to Darunavir that will allow for the easy production of derivative drug candidates. The discussion begins with our group’s development of a non-Evans syn- asymmetric glycolate aldol addition reaction that serves as the foundation of our proposed synthesis.
Recommended Citation
Witte, Jordan Michael, "An ( R )-4-Phenyl-1,3-oxazolidine-2-Thione Mediated Approach to 2, 3-Disubstituted Oxetanes and the Key Hydroxyethyl Isostere of the Hiv Protease Inhibitor Darunavir. Preparation of Non-evans Syn Glycolate Aldol Addition Products. a New Direction for the Curtius Rearrangement in the Dehomologation of Alpha-alkoxycarboxylic Acids" (2023). Theses and Dissertations. 1714.
https://ir.library.illinoisstate.edu/etd/1714
DOI
https://doi.org/10.30707/ETD2023.20230711063203283312.999937
Page Count
173