New Approaches for Efficiency in Synthetic Organic Chemistry

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With the support of the Organic and Macromolecular Chemistry Program, Professor Barry M. Trost, of the Department of Chemistry at Stanford University, is developing new and efficient approaches for the synthesis of complex organic molecules. He is exploring a number of palladium, platinum, and ruthenium-catalyzed transformations, including the synthesis of skipped and conjugated dienes, butenolides with unsaturated side chains, and cross-conjugated trienes, the isomerization of propargylic alcohols to enals, and the isomerization of ynals to unsaturated esters. Multicomponent cyclizations afford efficient access to a variety of functionalities. Catalytic enantioselective pi-allyl palladium, molybdenum, ruthenium, and tungsten-based methodologies will be designed and developed, with the choice of metal dictating both the chemical and the stereochemical outcomes. Novel cyclization strategies based on nucleophilic catalysis are opening new doors for unprecedented approaches to polypeptide synthesis.As our knowledge of the structure and reactivity of molecules increases, the practice of organic synthesis is undergoing a change in focus, with the question now more often asked being not if a complex target can be synthesized, but rather how. Practical syntheses derive from the existence of a basic set of synthetic reactions, and the limitations of that base set define the extent to which organic syntheses may be made economical, efficient, and environmentally conscious. With the support of the Organic and Macromolecular Chemistry Program, Professor Barry M. Trost, of the Department of Chemistry at Stanford University, is developing new and selective reactions which add to our arsenal of techniques for the synthesis of the complex organic molecules increasingly forming the basis of a myriad of applications, ranging from biology to materials science.