The Cover

Our cover is derived from this issue's Viewpoints article on organic and natural products synthesis by Nicolaou, Sorensen, and Winssinger (page 1225*). It shows a Pacific yew tree with the molecular structure of taxol, a potent anticancer drug, superimposed over it. Because extraction of taxol requires sacrifice of one 100-year-old tree for each dose of the drug, synthesizing taxol is of great interest. Taxol is currently obtained by semisynthesis (synthesis that begins with a closely related natural product) from needles of the European yew. It has also been produced by total synthesis by five independent pathways.

Organic Synthesis

In addition to the Viewpoints article, this issue contains a wealth of information about organic synthesis. Several articles are aimed at advanced undergraduate courses. Cannon and Krow (page 1259) have used synthesis of complex natural products as the basis for a student-centered, problem-based laboratory course that involves group learning. Augé and Lubin-Germain (page 1285) provide an experiment in which chemical synthesis and two-dimensional NMR are combined. Thin-layer chromatography and liquid scintillation counting are used to evaluate enantiomeric purity by LeFevre (page 1287). Anoune et al. (page 1290) describe how MO theory can help students to interpret the results of Baeyer-Villiger oxidations.

An introductory organic lab developed by Perrine, Sabanayagam, and Reynolds (page 1266) involves preparation of "N-methyl-Prozac", an immediate precursor of the well-known antidepressant. A popular organic lab in which DEET, the active ingredient in many insect repellents, is synthesized has been modified by Knoess and Neeland (page 1267) so that students obtain a purer product. Olmsted (page 1261) describes a general chemistry experiment in which aspirin is synthesized. Production, extraction, and qualitative testing of penicillin are included in an experiment devised by Stevens and Billingsley (page 1264) for health-science courses. Synthesis is also touched on in a report from Nature by Heinhorst and Cannon (page 1207*) that describes chemistry related to malaria and red tides. Some of the red-tide chemistry appears in the Viewpoints paper as well (pages 1245-1250*).

Natural Products and Biochemistry

A number of papers involve natural products and biochemical systems. Cousins and Pierson have developed a microscale method for extracting pigments from spinach (page 1268*) that reduces the quantity of solvent needed and the time required for the experiment. Use of enzymes to convert carbohydrate wastes into fuel is described by Hershlag, Hurley, and Woodward (page 1270*). This would be suitable for introductory courses emphasizing environmental chemistry or biochemistry. Anderson and McNellis (page 1275*) have developed an experiment for introductory biochemistry that shows how enzyme-linked antibodies can be used as a tool for assays that can detect femtomolar (10^-15 M) concentrations.

Allison and Bering (page 1278) have developed a biochemistry laboratory on immobilized enzyme technology and how it can be effective in industrial processes. Martin (page 1281) has developed an introductory biochemistry experiment in which baker's yeast is used in studies of metabolic activity. Peterman, Lentz, and Duncan (page 1283) describe an experiment that shows how ¹⁹F NMR can be used as an analytical tool in biochemical studies.

History and Chemistry

This month's Viewpoints paper shows that in many cases the use of a natural product preceded its isolation and synthesis by many years. Historical anecdotes can generate student interest and provide a humanizing factor in many courses. Lin (page 1326*) argues that history can be used effectively to teach atomic theory, and provides statistical evidence that this is so. Giunta (page 1322*) describes how a historical case study can be used to teach the scientific method. Rodygin and Rodygina (page 1320*) have developed a course in the early history of chemistry for liberal arts undergraduates. How chemists can apply their knowledge and experience to restoring and preserving cultural heritage (restoration of a vandalized Roman mosaic) is the subject of a fascinating story by Ciliberto et al. that begins on page 1302*. History, as told by someone who was directly involved in part of the tale, is provided by Davenport (page 1211*) in the story of Linus Pauling's interactions with the American Chemical Society.

Developing Students' Professional Skills

Skills that students will need on the job can be developed in a number of ways. That research is not foreign to two-year colleges and can carry over to internships and co-op assignments is demonstrated nicely by Whipple-VanPatter on page 1210*. Dunn, Kagi, and Phillips (page 1313) describe a third-year course on chemistry and technology that includes strong professional components. Issues in scientific integrity and ethics are the subject of a course developed by Rytting and Schowen (page 1317). To obtain feedback regarding the efficacy of an undergraduate chemistry program, Dreisbach et al. (page 1330) developed an assessment based on focus groups and exit interviews.

* designates articles of
special interest
to high school teachers.