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Date of Award

6-4-2014

Document Type

Thesis and Dissertation-ISU Access Only

Degree Name

Master of Science (MS)

Department

Department of Chemistry

First Advisor

Shawn R. Hitchcock

Abstract

Acyl succinimides represent a class of acyl transfer reagents that have not been studied extensively. This thesis describes the synthesis of acyl succinimides by the Steglich reaction and and application of acyl succinimides in the formation of amides under mild conditions. The acyl succinimides were also applied in a two-step, one-pot reaction sequence to efficiently form substituted amines. This work culminated in the synthesis of the first generation calcimimetic agent NPS-R-568 and the second generation calcimimetic agent cinacalcet.

Research was also carried out on the related acyl phthalimide reagents in the pursuit of enhanced reagents for the Nefkens' phthaloylation reaction. These phthalimide reagents included N-acyl-, N-methanesulfonyl-, and N-diphenylphosphinoylphthalimides. The N-acetylphthalimide yielded divergent reaction pathways depending on reaction conditions. The reaction either followed a pathway of acyl transfer or direct phthaloylation depending on the presence of the base triethylamine. The reagent that proved to be the most efficient in the Nefkens' reaction was the N-propanoylphthalimide.

Finally, a research program involving the total synthesis of a proposed human T-cell leukemia virus protease inhibitor was launched. Retrosynthetically, the protease inhibitor was divided into two main components, a chiral b-aminoalcohol and a tripeptide. The desired b-amino alcohol employed the Crimmins' asymmetric glycolate aldol reaction. The tripeptide is proposed to be prepared using an acyl succinimide approach.

Comments

Imported from ProQuest Goodman_ilstu_0092N_10295.pdf

Page Count

303

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