UC San Diego

Natural products, or secondary metabolites of plants and animals, have proven invaluable to humanity. We have used them for myriad reasons throughout history, including non- essential purposes such as dyes for textiles and paints. Less trivial uses, such as those related to food and health better demonstrate the importance of natural products. We have made use of toxic natural products to bolster hunting efficiency (e.g. poison tipped darts), and insect pheromones and natural products with antifeedant properties have assisted agricultural growth. Therapeutic natural products have long been used as dietary supplements and medicines. The ubiquitous nature of natural products and their derivatives in current health care validates continued laboratory work in all areas of natural product research. We (The Theodorakis Lab) have viewed natural product synthesis as a tool for expanding our understanding of organic chemistry. Of particular interest, are natural products which contain rare or novel architectural features. The synthetic study of these natural products therefore inspires creative solutions to complicated synthetic challenges, and often necessitates the development of new methodologies. Unique structural characteristics of two natural product families, Schisandraceae dilactones and zoanthamine alkaloids, caught our interest for the stated reasons. Research herein describes work directed towards synthesis of the unprecedented micrandilactone A ABC ring system and a distinctive approach to the zoanthamine alkaloids. Chapter I narrates research related to the micrandilactone A ABC ring motif which culminated in an interesting multi-step one pot acid mediated reaction for AC ring formation. Chapter II reports attempts at poly-cyclization cascade reactions directed toward zoanthamine alkaloid synthesis