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Title:Studies on the Total Synthesis of (+/-)-Cameroonan-7alpha-Ol and Presilphiperfolan-8-Ol and Discovery of a Novel Stereoselective Prins Cyclization of Delta,epsilon-Unsaturated Ketones
Author(s):Davis, Chad Eric
Doctoral Committee Chair(s):Coates, Robert M.
Department / Program:Chemistry
Discipline:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Degree:Ph.D.
Genre:Dissertation
Subject(s):Chemistry, Organic
Abstract:A novel stereoselective Prins cyclization reaction of unsaturated ketones was discovered. It was found that reaction of TiCl4 with delta,epsilon- or epsilon,zeta-unsaturated ketones at low temperature followed by buffered methanolysis provided monocyclic and bicyclic cis 3-chlorocyclohexanols. Testing of ten unsaturated ketones and four acid activators provided evidence for substrate generality while the stereoselectivity was rationalized by intramolecular delivery of the nucleophile.
Issue Date:2003
Type:Text
Language:English
Description:290 p.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 2003.
URI:http://hdl.handle.net/2142/84098
Other Identifier(s):(MiAaPQ)AAI3086042
Date Available in IDEALS:2015-09-25
Date Deposited:2003


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