2012 Theses Doctoral

Strategic Applications of Tandem Reactions in Complex Natural Product Synthesis: Rapid Access to the (Iso)Cyclocitrinol Core

Plummer, Christopher Wainwright

This thesis describes the efforts of Professor James Leighton and myself toward the synthesis of the tetracyclic core of a class of steroidal natural products known as the cyclocitrinols.

Our initial work in this area was performed on racemic model systems in order to validate our ring contraction-Cope rearrangement strategy. Novel chemistry was then identified to access the functionalized core in enantio-enriched form.

Finally, in line with our efforts to probe the transition state of our key tandem Claisen-Cope reaction, additional substrates were prepared supporting our proposed transition state and improving the efficiency of this transformation.