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

Davis, Chad Eric

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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