Asymmetric hydration: Applications to RK-397 and virginiamycin

ORGN 73

Matthew S. Mortensen, mort0110@gmail.com and George A. O'Doherty, george.odoherty@mail.wvu.edu. C. Eugene Bennett Department of Chemistry, West Virginia University, PO Box 6045, Morgantown, WV 26505
Using the asymmetric hydration sequence developed in our labs two important natural products are now being targeted for synthesis, RK-397 and virginiamycin. Combined with the Leighton allylation procedure, our asymmetric hydration allows us to set nearly all the stereocenters in RK-397 and virginiamycin. The starting materials for this efficient reaction sequence are simple, achiral conjugated dienoates, which are converted rapidly into complex enantio-enriched building blocks for natural products like RK-397 and virginiamycin.