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Graduation Term
2020
Degree Name
Master of Science (MS)
Department
Department of Chemistry
Committee Chair
Shawn Hitchcock
Abstract
The Human T cell leukemia virus (HTLV-1) has been established as the first retrovirus to be directly associated with human malignancy. A commonality between HTLV-1 and other retroviruses is that it encodes a protease (PR) necessary for it to mature. Building upon the synthetic model of the known protease of HTLV-1 established by Aimoto and co-workers, Kenichi Akaji and co-workers were able to synthesize a protease inhibitor that successfully interacted with the protease. We became interested in the asymmetric synthesis of the Akaji protease inhibitor for the HTLV-1 using an oxazolidine-2-thione directed asymmetric glycolate aldol addition route in other to have a shorter and efficient synthesis. Once this process was successfully completed, we proceeded to reductively cleave the chiral auxiliary to generate the corresponding diol that was chemoselectively sulfonylated with p-toluenesulfonyl chloride. Treatment of this system with a variety of nucleophiles resulted in oxetane derivative formation. After numerous attempts to open the oxetane derivative minor product, an alternate pathway of transamidation was pursued.
Access Type
Thesis-ISU Access Only
Recommended Citation
Addo, Marian Aba, "Efforts towards the Formal Synthesis of the Akaji Human T-cell Leukemia Virus Type 1 ( Htlv-1 ) Protease Inhibitor via an Asymmetric Glycolate Aldol Addition Route" (2020). Theses and Dissertations. 1273.
https://ir.library.illinoisstate.edu/etd/1273
DOI
https://doi.org/10.30707/ETD2020.1604319238862