Research Interests

My research interests are in the area of synthetic organic chemistry, both in the development of new synthetic methods and in the exploration of new strategies for the synthesis of complex molecules. In the late 1970s, my students and I began a detailed investigation of the factors that govern the stereochemical outcome of the lithium enolate aldol addition reaction. These studies pointed out a strong correlation between enolate geometry and aldol relative configuration and led to the widespread use of the aldol addition reaction as a tool for "acyclic stereocontrol." Our initial studies of the aldol reaction were later extended to a similar investigation of the lithium enolate Michael addition reaction. In recent years my interests have moved more in the direction of multistep synthesis of complex organic molecules, usually natural products. A powerful synthetic strategy that we have been investigating is "biomimetic synthesis," in which we try to deduce synthetic routes purely from an examination of structural relationships within a family of structurally related secondary metabolites. That is, the mere coexistence of several related structures suggests that there exists a feasible chemical pathway between the structures. On occasion, we have been able to demonstrate these pathways in the laboratory. One example of the power of this approach to synthesis was our discovery in 1990 of a spectacular cascade of reactions leading from an acyclic derivative of squalene to the pentacyclic alkaloid proto-daphniphylline.

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Section 14: Chemistry