Enantioselective synthesis of Goniothalamin Oxide

ORGN 168

George A. O'Doherty, george.odoherty@mail.wvu.edu and Philip Ryan Harsh, pharsh@mix.wvu.edu. C. Eugene Bennett Department of Chemistry, West Virgnia University, 284 Prospect Street, 217 Clark Hall, Morgantown, WV 26506
The enatioslective synthesis of Goniothalamin Oxide has been achieved in 5 steps from achiral cinnamaldehyde. The route relies upon a diastereoselective Leighton allylation to establish the desired C-5 stereochemistry. This route also relies on a ring-closing metathesis to establish the α,β-unsaturated lactone and a hydroxyl- directed epoxidation to stereoselectively install the epoxide. Our efforts to combine Goniothalamin Oxide with Altholactone to form Goniolactone A are ongoing and our latest results will be discussed.