Tandem Diels-Alder/ene reaction: Total synthesis of Isoligularone

ORGN 531

Jaehoon Bae, jaehoon2@iastate.edu and George A. Kraus, gakraus@iastate.edu. Department of Chemistry, Iowa State University, Ames, IA 50014
Recently, we have developed Lewis acid catalyzed tandem Diels-Alder/ene reactions as a facile route to generate bicyclic building blocks. Since this tandem reaction creates up to five stereogenic centers in a single operation, the core structure of eremophilane sesquiterpenes can be easily synthesized. In this poster, we will present the use of tandem Diels-Alder/ene reaction as the key step in our synthesis of isoligularone.