Raymond E. Forslund

Intramolecular Oxamidation of Unsaturated O-Alkyl Hydroxamates: A Remarkably Versatile Entry to Hydroxy Lactams

The development of a versatile method for the preparation of five- to eight-membered hydroxy lactams that involves the iodine(III)-mediated oxamidation of unsaturated O-alkyl hydroxamates is described. This transformation, which is believed to proceed through the intermediacy of singlet nitrenium and bicyclic N-acyl-N-alkoxyaziridinium ions, is both stereospecific and highly regioselective in most of the 22 cases examined.

Synthesis of (′)-7-episordidin

Abstract The stereoselective synthesis of (±)-7-episordidin, an aggregation pheromone from the male banana weevil, Cosmopolites sordidus Germar, is reported. The key step of this work is a regioselective rhodium(II)-catalyzed diazocarbonyl C H insertion reaction that simultaneously generates three of the natural products four stereocenters. The work reported herein also represents a formal synthesis of sordidin.

Development of a biochemistry laboratory course with a project‐oriented goal

A new course for undergraduate biochemistry laboratory has been developed in the Department of Chemistry at the University of Illinois at Chicago. The course is innovative pedagogically by giving students a set of relevant skills for biochemical research and then allowing them to apply those skills in designing and performing the procedures for a research‐like project. The course content focuses on the pharmacologically important enzyme β‐lactamase, which is involved in the hydrolysis of antibiotics such as penicillins and cephalosporins. Specifically, each student designs and performs site‐directed mutagenesis of the enzyme β‐lactamase and analyzes the effect of mutation on the catalytic function of the enzyme by an enzyme assay. This unique and valuable research experience greatly enhances their understanding of scientific reasoning and the research process. Evaluation of the progress also indicates successful linkage of skill‐building and student‐directed activities even for students with no prior experience.

Template-directed CH activation: development and application to the total synthesis of 7-episordidin

Abstract The development of a template-directed CH activation strategy and its application to the diastereoselective synthesis of (±)-7-episordidin, an aggregation pheromone from the male banana weevil, Cosmopolites sordidus Germar, is reported. The key step of the synthetic route is a regioselective rhodium(II)-catalyzed diazocarbonyl CH activation reaction that simultaneously generates three of the four stereocenters present in the natural product.