Hetero-Diels-Alder reactions of o-quinones

CHED 303

Deepika Nayyar, dnayyar@mail.csuchico.edu, Chris Taylor, taychr@gmail.com, and Jinsong Zhang, jzhang2@csuchico.edu. Department of Chemistry and Biochemistry, California State University, Chico, 400 West 1st St., Chico, CA 95929-0210
The inverse electron demand hetero-Diels-Alder reaction between ortho-quinones and enamines has the potential to be an effective and novel synthetic route to the 1,4-benzodioxane core of many natural products. These molecules display antibacterial and antiviral effects, but an efficient method for asymmetric synthesis has proven elusive. The application of this reaction to the stereoselective synthesis of the benzodioxane structure will be discussed.