Dissertations:
Strategic Applications of Tandem Reactions in Complex Natural Product Synthesis: Rapid Access to the (Iso)Cyclocitrinol Core
Christopher Wainwright Plummer
Downloads:
- Title:
- Strategic Applications of Tandem Reactions in Complex Natural Product Synthesis: Rapid Access to the (Iso)Cyclocitrinol Core
- Author(s):
- Plummer, Christopher Wainwright
- Thesis Advisor(s):
- Leighton, James L.
- Date:
- 2012
- Type:
- Dissertations
- Department:
- Chemistry
- Permanent URL:
- http://hdl.handle.net/10022/AC:P:12350
- Notes:
-
Supporting data available at http://hdl.handle.net/10022/AC:P:12353.
Ph.D., Columbia University. - Abstract:
- 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.
- Subject(s):
- Chemistry
- Item views:
- 74