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Date of Award
6-18-2020
Document Type
Thesis-ISU Access Only
Degree Name
Master of Science (MS)
Department
Department of Chemistry
First Advisor
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.
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
Page Count
112
Comments
Imported from ProQuest Addo_ilstu_0092N_11745.pdf