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City University of New York (CUNY)

Dissertations, Theses, and Capstone Projects

2014

Synthesis

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Oxocarbenium Ion And Alkene Metathesis Strategies For The Synthesis Of Complex Cyclohexanes, Clayton Errol Mattis Oct 2014

Oxocarbenium Ion And Alkene Metathesis Strategies For The Synthesis Of Complex Cyclohexanes, Clayton Errol Mattis

Dissertations, Theses, and Capstone Projects

Highly oxygenated cyclohexanes comprise the structures of a number of pharmacologically interesting molecules, including potently bioactive natural products and carbapyranosides. The latter, which are unnatural analogues of carbohydrates in which the ring oxygen of the parent sugar is replaced with a methylene group, have attracted interest as hydrolytically stable mimetics of their parent O-glycosides. This research reports the development of two general methodologies for the synthesis of highly oxygenated cyclohexanes: (1) Oxocarbenium Ion Cyclization (OCC) and (2) Ring Closing Metathasis (RCM).

Chapter one gives a review of the literature on the synthesis for highly oxygenated cyclohexanes.

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