Strategic Applications of Tandem Reactions in Complex Natural Product Synthesis
Subtitle: Rapid Access to the (Iso)Cyclocitrinol Core
By: Christopher Wainwright Plummer
Publisher: [publisher not identified]
Published: 2012
Place of publication: [New York, N.Y.?]
Language: eng
Description: 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.
Notes: Supporting data available at http://hdl.handle.net/10022/AC:P:12353.

Department: Chemistry.

Thesis advisor: James L. Leighton.

Thesis (Ph.D.)--Columbia University, 2012.