Date of Award
Doctor of Philosophy
George A. Kraus
The efficient construction of fused and bridged carbocyclic ring systems has always been a challenge for the organic chemist. We describe the following advances: (1) An effective method for making cis-fused cyclopentanoids using samarium diiodide has been achieved. The resulting tricyclic fused systems were utilized in two concise approaches to rocaglamide, a compound that exhibits significant antileukemic activity. (2) A novel way of constructing bridged ring systems involving a reactive enone intermediate and 1,1,3-trisubstituted dienes has been effected. The unusual preference for the exo mode of cycloaddition is explained.
Digital Repository @ Iowa State University, http://lib.dr.iastate.edu/
James Nicolas Ong Sy
Sy, James Nicolas Ong, "Synthesis of fused and bridged ring systems " (1988). Retrospective Theses and Dissertations. 9735.