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I. A New Synthetic Approach To The Synthesis Of N-(Phosphonoacetyl)-L-Ornithine, Ii. The Influence Of Pyridine On The Ozonolysis Of Alkenes, Bradley M. Johnson
I. A New Synthetic Approach To The Synthesis Of N-(Phosphonoacetyl)-L-Ornithine, Ii. The Influence Of Pyridine On The Ozonolysis Of Alkenes, Bradley M. Johnson
Department of Chemistry: Dissertations, Theses, and Student Research
Part I. The use of chemical inhibitors to manipulate the level of amino acids in cells has proven to be invaluable in the mechanistic study of gene expression in bacteria and fungi. Here we present a new approach to the synthesis of δ‐N‐ (phosphonoacetyl)‐L‐ornithine (PALO), a potent ornithine transcarbamylase inhibitor, using a new amino acid protecting group, 9‐borabicyclononane (9‐BBN). Starting from commercially available reagents and utilizing mild reaction conditions, we were able to form PALO in fewer synthetic steps and in greater yields than previous attempts.
Part II. Ozonolysis is widely used to transform alkenes into oxygen‐rich functional groups (e.g.– …
I. Development Of The In Situ Reductive Ozonolysis Of Alkenes With Tertiary Amine N-Oxides. Ii. Progress Toward The Asymmetric Synthesis Of Peroxyplakoric Acid A3., Christopher P. Schwartz
I. Development Of The In Situ Reductive Ozonolysis Of Alkenes With Tertiary Amine N-Oxides. Ii. Progress Toward The Asymmetric Synthesis Of Peroxyplakoric Acid A3., Christopher P. Schwartz
Department of Chemistry: Dissertations, Theses, and Student Research
Ozone, first discovered in the mid 1800’s, is a triatomic allotrope of oxygen that is a powerful oxidant. For over a century, research has been conducted into the synthetic application and mechanism of reactions of ozone with organic compounds. One of the major areas of interest has been the ozonolysis of alkenes. The production of carbonyl compounds is the most common synthetic application of ozonolysis. The generally accepted mechanism developed by Rudolf Criegee for this reaction involves the 1,3-electrocyclic addition of ozone to the π bond of the alkene to form a 1,2,3-trioxolane or primary ozonide. The primary ozonide is …