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Synthetic Studies Towards (+)-Dactylol Utilizing an Oxonium Ylide Rearrangement and Related Studies. Open Access


Other title
oxonium ylide
Type of item
Degree grantor
University of Alberta
Author or creator
Johnston, Jeffrey
Supervisor and department
West, Frederick (Chemistry)
Examining committee member and department
Glover, Mark (Biochemistry)
Hall, Dennis (Chemistry)
Clive, Derrick (Chemistry)
Hanna, Gabriel (Chemistry)
Harmata, Michael (Chemistry)
Department of Chemistry

Date accepted
Graduation date
Doctor of Philosophy
Degree level
Dactylol is a structurally interesting sesquiterpene natural product. One of its key structural features is an the eight-membered ring. The challenges of synthesizing an eight membered ring are discussed in Chapter 1. In addition, various methods for generating an eight-membered ring are highlighted within the several discussed total syntheses of dactylol. The West group has developed methodologies for generating eight membered rings that have utilized the rearrangement of an oxonium ylide. This method has been applied towards the total synthesis of dactylol. In Chapter 2, the previous synthetic routes as well as extensions to these routes are discussed. In addition, an advanced route towards the natural product has been developed and is examined in detail. In our approach towards the total synthesis of dactylol, we discovered a side product during a dicyclohexylcarbodiimide esterification reaction. This side product was determined to be an imino-oxazinone. The synthesis of these heterocycles has been developed using an in situ generated acyl ketene, which undergoes a formal [4+2] cycloaddition with a carbodiimide. This convergent approach has been applied to several different acyl ketenes and carbodiimides and is discussed in Chapter 3. 4 During our studies of dactylol we became interested in the Stevens rearrangement of an oxonium ylide with an adjacent cyclopropylcarbinyl group. This rearrangement substrate has not been previously investigated and is interesting as it would give valuable mechanistic information on the Stevens rearrangement. The preliminary investigations into these compounds are discussed in Chapter 4.
Permission is hereby granted to the University of Alberta Libraries to reproduce single copies of this thesis and to lend or sell such copies for private, scholarly or scientific research purposes only. Where the thesis is converted to, or otherwise made available in digital form, the University of Alberta will advise potential users of the thesis of these terms. The author reserves all other publication and other rights in association with the copyright in the thesis and, except as herein before provided, neither the thesis nor any substantial portion thereof may be printed or otherwise reproduced in any material form whatsoever without the author's prior written permission.
Citation for previous publication
Murphy, G. K. Ph. D. Thesis. University of Alberta, 2007.

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