Efforts toward the divergent asymmetric total syntheses of Xenia diterpenoids

ORGN 156

Timothy S. Snowden, snowden@bama.ua.edu, Murali K. Urlam, urlam@bama.ua.edu, and Jeremy Carr, carr030@bama.ua.edu. Department of Chemistry, The University of Alabama, Box 870336, Tuscaloosa, AL 35487-0336
Xenia diterpenoids are secondary metabolites isolated from the crude organic extracts of brown algae or coelenterates. Xenia diterpenoids feature a 6,7-trisubstituted (E)-cyclononenone ring attached to trans-fused substituents at C2 and C3. Since their initial isolation and characterization in 1977, these natural products are now widely recognized as molecules that offer an enticing array of cytotoxic, antitumor, anti-angiogenic, antifungal, antibacterial, and anti-inflammatory activities of commendable potency. However, in no instance has a mode of action been established. We wish to present here our efforts toward the asymmetric synthesis of an advanced common intermediate from commercially available starting materials. This intermediate will be employed in the divergent asymmetric total synthesis of several biologically active Xenia diterpenoids.