The two primary functions of synthetic organic chemistry, as a discipline, are making small molecules of known importance more efficiently and making potentially useful, previously inaccessible molecules. The Diels–Alder reaction serves as an ideal tool in the synthetic chemist’s toolbox because it enables both of these goals. Since its discovery in 1928, the mechanism of the Diels–Alder reaction has been investigated, the synthetic scope has been expanded, and the reaction has been applied to a vast number of challenging synthetic problems. By contrast, the analogous Wagner-Jauregg reaction, discovered only two years after the Diels–Alder reaction was first reported, has received very limited attention. Long considered a special type of Diels–Alder reaction, in which a styrenyl diene is utilized, very few attempts to apply this reaction to the synthesis of complex small-molecules have been reported. In this presentation, I will report on preliminary studies to support or refute the proposed reaction mechanism and will showcase efforts towards expanding the scope of the Wagner-Jauregg reaction.

Exploring the Wagner-Jauregg reaction

256th National Meeting (2018)

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