Studies on the structure/reactivity relationships of bicyclic epoxonium ions toward tethered nucleophiles

ORGN 32

Shuangyi Wan, shw5@pitt.edu and Paul E. Floreancig, florean@pitt.edu. Department of Chemistry, University of Pittsburgh, 219 Parkman Ave, Pittsburgh, PA 15260
A systematic study on the structure/reactivity relationships of bicyclic epoxonium ions towards tethered nucleophiles has been conducted. The cyclization results show that bicyclo[4.1.0] epoxonium ions have a strong preference for endo-cyclization while bicyclo[3.1.0] epoxonium ions have a significant to exclusive preference for exo-cyclization. This method is currently being applied to the total synthesis of (-)-lactodehydrothyrsifeol.

 

New Reactions and Methodology
8:00 AM-12:00 PM, Sunday, April 6, 2008 Morial Convention Center -- Rm. R04, Oral

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008