The focus of this research is the development of a double annulation strategy for the preparation of bicyclo(4.n.0)alkanes with multiple functionality and substitution. The utility of the method, which employs a tandem Michael, Dieckmann sequence, will be showcased by the preparation of a number of interesting polyterpenoids. The focus of the educational activities is on course development featuring the use of web-based, interactive homework and essay assignments. With this Faculty Early Development (CAREER) award, the Organic and Macromolecular Chemistry Program is supporting the research and educational activities of Dr. Robert B. Grossman of the Department of Chemistry at the University of Kentucky. Professor Grossman will focus his research efforts on developing synthetic methodology useful in the preparation of organic compounds having interesting biological properties. The educational component of the award will stress course development in undergraduate organic chemistry.