Strategic Applications of Tandem Reactions in Complex Natural Product Synthesis: Rapid Access to the (Iso)Cyclocitrinol Core
Christopher Wainwright Plummer
- Strategic Applications of Tandem Reactions in Complex Natural Product Synthesis: Rapid Access to the (Iso)Cyclocitrinol Core
- Plummer, Christopher Wainwright
- Thesis Advisor(s):
- Leighton, James L.
- Permanent URL:
Supporting data available at http://hdl.handle.net/10022/AC:P:12353.
Ph.D., Columbia University.
- 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.
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