Progress toward a total synthesis of Maoecrystal V

ORGN 742

Douglas D. McLeod, dmcleod@princeton.edu, William J. Chain, wchain@princeton.edu, and Erik J. Sorensen, ejs@princeton.edu. Department of Chemistry, Princeton University, Washington Rd., Princeton, NJ 08544
The potent and selective anticancer compound, maoecrystal V, was isolated in 2004 from the perennial herb or shrub Isodon eriocalyx (Dunn.) Hara. As an unprecedented and highly modified C19 Isodon ent-kauranoid, the complex, pentacyclic topology of maoecrystal V poses a challenge to synthetic chemistry. Progress toward a concise synthesis of this natural product and a rapid development of the core structure is described.