With this CAREER Award, the Chemical Synthesis program is supporting the research of Professor Jiong Yang of Texas A&M University. Professor Yang will develop efficient synthetic approaches to zoanthamines, a family of complex polycyclic marine alkaloids possessing biological properties that are valuable for therapeutic applications. First, a transannular Michael reaction cascade will be systematically explored to elucidate its scope and stereochemical outcome for synthesis of polycyclic molecular structures. Second, the total synthesis of norzoanthamine, an anti-osteoporotic member of natural products of the zoanthamine family, will be completed. The transannular Michael reaction cascade will be employed to synthesize its stereochemically complex and highly functionalized ABC ring system. Other cascade reactions will also be developed for efficient assembly of the complex polycyclic molecular skeleton of zoanthamines. For the final objective, a synthetic route to 28-deoxyzoanthenamine will be developed based on a proposed biosynthetic scheme.
Professor Yang will also initiate educational projects that interweave research and teaching. The first project involves an outreach program targeting local high school science educators by providing opportunities for professional development through discovery-based research in his laboratory. The second initiative involves outreach to K-12 students through a Chemistry Laboratory Open House program to share the excitement of scientific research/discoveries and encourage these students to consider exploring STEM fields.
Under the support of this NSF grant, an important accomplishment was the principle investigator’s successful development of a method for efficient chemical synthesis of organic structures with some very challenging three-dimensional structures. These structures have been found in natural products, such as zoanthamines, that have potential medical applications. The three-dimensional arrangement of atoms of these structures is important because such arrangement is necessary for interacting with biological molecules, such as proteins, that are relevant to the medical conditions. Due to their complex three-dimensional molecular structures, these natural products had been difficult to prepare using existing synthetic methods, they had also been difficult to obtain from Nature without a major impact to the environment due to the scarcity of their natural producers (some rare marine animals in the case of zoanthamines). Thus, an efficient synthetic method that would allow chemical synthesis of these natural products is critically important for obtaining these rare organic compounds, and enable subsequent studies to explore their potential use that benefit the society. Following the development of this synthetic method, the principle investigator successfully applied this method to synthesize a significant portion of norzoanthamine, a highly complex zoanthamine natural product with potent anti-osteoporotic properties. This NSF grant also enabled the principle investigator to engage in outreaching activities with local K12 students through participation in TAMU Chemistry Open House.
