2012 Theses Doctoral
Strategic Applications of Tandem Reactions in Complex Natural Product Synthesis: Rapid Access to the (Iso)Cyclocitrinol Core
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.
- Plummer_columbia_0054D_10492.pdf application/pdf 3.43 MB Download File
More About This Work
- Academic Units
- Thesis Advisors
- Leighton, James L.
- Ph.D., Columbia University
- Published Here
- January 27, 2012
Supporting data available at http://hdl.handle.net/10022/AC:P:12353.