Pericyclic reaction cascades in biomimetic total synthesis

ORGN 723

Jeremiah P. Malerich, jmalerich@berkeley.edu and Dirk Trauner. Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720
Pericyclic reaction cascades have been used to generate complex structures with excellent stereoselectivity and atom-economy in a single operation. The application of electrocyclization and cycloaddition tandem reactions to naphthoquinones from Bignoniaceae and the sesquiterpene lactone xanthipungolide is presented. The implications on the biosynthesis of the natural products and the discovery of catalysis of oxa-electrocyclizations is described as well.