Cyclization synthetic approach to the C19 quassinoids

ORGN 915

Valerie A. Cwynar, cwynar.2@osu.edu, Matthew G. Donahue, mdonahue@chemistry.ohio-state.edu, and David J. Hart, hart.10@osu.edu. Department of Chemistry, The Ohio State University, Columbus, OH 43210
The C19 quassinoids are a small family of terpenoids exemplified by polyandrane. This paper will describe a synthetic approach in which a cycloetherification provides the E/C ring system, and a 5-exo-dig radical cyclization gives the B ring (12). Efforts to convert 2 and related structures to the polyandranes will also be described.