atmire.migration.oldid	2784
dc.contributor.advisor	Back, Thomas
dc.contributor.author	Johnson, Aaron
dc.date.accessioned	2014-12-15T23:12:40Z
dc.date.available	2015-02-23T08:00:34Z
dc.date.issued	2014-12-15
dc.date.submitted	2014	en
dc.description.abstract	The potent anti-inflammatory agent, BIRT-377, contains an α-quaternary center in a hydantoin ring. Due to requirements for clinical testing on enantiopure compounds, the need for enantioselective routes to chiral compounds, such as BIRT-377, are highly sought. Enantioselective syntheses of compounds containing α-quaternary amine moieties are difficult because steric hinderance precludes the use of many standard synthetic procedures. Enzymatic desymmetrization of α,α-disubstituted malonic esters, followed by Curtius rearrangement, has been shown to provide access to α-quaternary amino acid derivatives, often with high enantiopurity. Thus, using this methodology a stereodivergent synthesis of BIRT-377 was accomplished, affording both enantiomers in high optical purity. Acetylenic sulfones have been employed in sequential conjugate addition and cyclization reactions in our group to synthesize various nitrogen-containing heterocycles. We attempted to extend this methodology to the synthesis of the alkaloid gephyrotoxin; however, we were unable to obtain a β-amino ester compound required for a key conjugate addition step.	en_US
dc.identifier.citation	Johnson, A. (2014). A Stereodivergent Synthesis of the Anti-Inflammatory Agent BIRT-377. Approaches to the Synthesis of Gephyrotoxin (Master's thesis, University of Calgary, Calgary, Canada). Retrieved from https://prism.ucalgary.ca. doi:10.11575/PRISM/25038	en_US
dc.identifier.doi	http://dx.doi.org/10.11575/PRISM/25038
dc.identifier.uri	http://hdl.handle.net/11023/1961
dc.language.iso	eng
dc.publisher.faculty	Graduate Studies
dc.publisher.institution	University of Calgary	en
dc.publisher.place	Calgary	en
dc.rights	University of Calgary graduate students retain copyright ownership and moral rights for their thesis. You may use this material in any way that is permitted by the Copyright Act or through licensing that has been assigned to the document. For uses that are not allowable under copyright legislation or licensing, you are required to seek permission.
dc.subject	Chemistry--Organic
dc.subject.classification	BIRT-377	en_US
dc.subject.classification	Gephyrotoxin	en_US
dc.subject.classification	Synthesis	en_US
dc.subject.classification	Enantioselective	en_US
dc.subject.classification	Stereodivergent	en_US
dc.title	A Stereodivergent Synthesis of the Anti-Inflammatory Agent BIRT-377. Approaches to the Synthesis of Gephyrotoxin
dc.type	master thesis
thesis.degree.discipline	Chemistry
thesis.degree.grantor	University of Calgary
thesis.degree.name	Master of Science (MSc)
ucalgary.item.requestcopy	true

A Stereodivergent Synthesis of the Anti-Inflammatory Agent BIRT-377. Approaches to the Synthesis of Gephyrotoxin

Files

Original bundle

License bundle

Collections

Libraries & Cultural Resources