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Preparation of para-disubstituted benzenes, formation of optically pure cyclic amines by intramolecular conjugate displacement and total synthesis of marinopyrrole B Open Access


Other title
para-disubstituted benzenes
marinopyrrole B
intramolecular conjugate displacement
optically pure cyclic amines
Type of item
Degree grantor
University of Alberta
Author or creator
Cheng, Ping
Supervisor and department
Clive, Derrick L. J. (Chemistry)
Examining committee member and department
Kaur, Kamaljit (Pharmacy and Pharmaceutical Sciences)
Ciufolini, Marco (Chemistry, University of British Columbia)
Bundle, David R. (Chemistry)
Vederas, John C. (Chemistry)
Bergens, Steven H. (Chemistry)
Department of Chemistry

Date accepted
Graduation date
Doctor of Philosophy
Degree level
The first chapter of this thesis describes a method for making para-disubstituted benzenes. The process involves reaction of acetylides with aldehydes to give 1,4-diols, triple bond reduction and oxidation of the resulting 1,4-diols to 1,4-diketones. Treatment of the 1,4-diketones with vinylmagnesium bromide, followed by ring-closing metathesis and dehydration, affords para-disubstituted benzenes. The method was applied to the synthesis of C5-aryl carbohydrates. The second chapter describes an intramolecular conjugate displacement (ICD) between a nitrogen nucleophile and a Morita-Baylis-Hillman acetate with a chiral auxiliary for making optically pure cyclic amines. Removal of the chiral auxiliary from the ICD products with DIBAL-H provides optically pure six- or seven-membered cyclic amines having a stereogenic center α to nitrogen. The last chapter of this thesis describes the first total synthesis of the marine antibiotic alkaloid, marinopyrrole B, which shows very strong activity against methicillin-resistant Staphylococcus aureus. It is known that marinopyrrole B can not be made directly by bromination of marinopyrrole A, and so bromination of one pyrrole unit at an early stage was the basis of my successful route. The nitrogen of the brominated pyrrole was alkylated with a Michael acceptor having an allylic leaving group, and the product was then modified to construct the second pyrrole via a Paal-Knorr reaction. The nitrogen of the resulting 1,3'-bipyrrole was then protected, followed by addition of an appropriate Grignard reagent, oxidation and deprotection reactions, to obtain a 1,3'-bipyrrole with two aromatic carbonyl groups. Finally, dichlorination and demethylation generated racemic marinopyrrole B.
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.
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