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Date of Award


Document Type

Thesis-ISU Access Only

Degree Name

Master of Science (MS)


Department of Chemistry

First Advisor

Shawn Hitchcock


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.


Imported from ProQuest Addo_ilstu_0092N_11745.pdf


Page Count


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