Abstract

The first project in this dissertation endeavors to outline the total synthesis of yaku'amide A and its analogs. Yaku'amide A is a natural product comprised of dehydroamino acids, including E-dehydro isoleucine, and unprecedented Z-dehydro isoleucine. These amino acids present a significant challenge to their synthesis owing to their unsymmetrical nature. To simplify the synthesis process, we synthesized analogs by substituting the E and Z dehydroamino acids with symmetrical subunits. This substitution facilitated the synthesis process and enabled us to obtain a similar three-dimensional structure to that of the natural product. Furthermore, biological testing of the simplified analogs revealed potency similar to yaku'amide A. The second part of this project describes the synthesis of the bicycle core of virosinine A, commencing with an enantioselective Evans glycolate aldol reaction. Following a series of transformations, an oxime phenyl ether is generated, which, upon microwave irradiation, triggers an iminyl radical cascade reaction. The iminium formed in the microwave reactor is reduced with red-Al, obtaining the desired diastereomer.

Degree

PhD

College and Department

Physical and Mathematical Sciences; Chemistry and Biochemistry

Rights

https://lib.byu.edu/about/copyright/