The study of N-acylpyridinium salt chemistry and its application in the asymmetric synthesis of Streptomyces SS20846A

by Homer, Holly K.

Homer, Holly K.: Study of N-Acylpyridinium Salt Chemistry and Its Application in the Asymmtric Synthesis of Streptomyces SS20846A. (Under the direction of Dr. Daniel L. Comins) The first part of this research was directed towards a study of the mechanism of N-acylpyridinium salt chemistry. Comparison of de’s obtained from organometallic additions to the pyridinium salt versus analogous non-organometallic additions would show whether chelation of the metals plays a key role in the mechanism. The second focus of this research was on the use of chiral N-acylpyridinium salt chemistry in the asymmetric synthesis of Streptomyces SS20846A, a natural product isolated from a soil sample in Greece which has a restrictive action on the digestive system. The Study of N-Acylpyridinium Salt Chemistry and Its Application in the Asymmetric Synthesis of Streptomyces SS20846A By Holly K. Homer A Thesis submitted to the Graduate Faculty of North Carolina State University in partial fulfillment of the requirements for the degree of Master of Science Department of Chemistry Raleigh, North Carolina 2000 Approved by: _____________________________ Dr. Daniel L. Comins, Chair ___________________________ Dr. Suzanne T. Purrington _________________________ Dr. Binghe Wang ii Biography The author, Holly K. Homer, was born in St. Mary, Ohio, on September 15, 1974 to Rev. Edwin and Margaret Homer. She grew up in Sheboygan, Wisconsin where she attended Sheboygan North High School and graduated in 1993. She studied chemistry at Evangel College in Springfield, Missouri, and graduated in 1996 with a Bachelor of Science degree. Holly attended North Carolina State University and completed her Master of Science degree in Synthetic Organic Chemistry in the spring of 2000 under the direction of Dr. Daniel L. Comins. iii