Professor Howell's research focuses on the synthesis of 2-alkylideneoxetanes and their use as potential inhibitors of serine and cysteine proteases as well as precursors for the synthesis of medium-ring carbocyclic compounds and spiroketals. Compounds bearing structural analogy to simple insect pheromones will be prepared using the latter methodology, which is designed to be simple and chemoselective, without extensive use of protecting groups, while proceeding under mild conditions. Approaches to other functionalities through the intermediacy of 2-alkylideneoxetanes will also be explored, as will the polymerization of 2-alkylideneoxetanes, expected to yield polyketones. Professor Howell will seek to facilitate student and faculty interactions with industry in order to achieve three goals: (1) to increase student appreciation of industrial career opportunities, (2) to improve faculty understanding of how to assist students with their job searches, and (3) to foster academic-industrial and industrial-academic collaborations. With this CAREER award, the Synthetic Organic Program supports the research and educational activities of Dr. Amy Howell of the Department of Chemistry at the University of Connecticut. Professor Howell examines the chemistry of a class of versatile precursor molecules that, to this point, have received little attention from the synthetic community. These compounds, comparatively small in size but containing a number of reactive groupings of atoms, permit synthetic access to a wide range of important compounds, including molecules anticipated to display unusual biological activity, as well as polymeric materials. Professor Howell's educational activities target the enhancement of student awareness of career opportunities in industry and the development of faculty-industry collaborations through workshops, in-house courses taught by industrial chemists, and internships in academic and industrial laboratories.