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dc.contributor.authorZiegler, Robert
dc.date.accessioned2016-02-23T15:10:29Z
dc.date.available2016-02-23T15:10:29Z
dc.date.issued2016
dc.identifier.urihttps://hdl.handle.net/2144/14556
dc.description.abstractPleiomaltinine is an alkaloid-pyrone natural product that was the first of its kind to be isolated in nature. Synthesis of this compound from pleiocarpamine and a reactive quinone methide-like pyrone is described. Furthermore, model compounds have been made that will allow for full testing of this new heterocycle’s biological properties. This process has also been rendered enantioselective using asymmetric organocatalysis with thioureas. Additionally, work has been conducted towards the total synthesis of vinylallene-derived natural products. Progress towards the syntheses of chloropupukeananin, chloropestolide A, pestalofone C, iso-A82775c, and maldoxin isolated from Pestalotiopsis fici are described. All of these compounds are complex and possess biological activities including anti-cancer and anti-HIV. The strategies applied to develop a selective synthesis of reactive vinylallenes are discussed and plans designed to overcome this synthetic challenge are shown in detail. New methodologies are presented along with literature precedent in these areas of research.en_US
dc.language.isoen_USen_US
dc.rightsAttribution 4.0 International
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.subjectChemistryen_US
dc.subjectOrganocatalysisen_US
dc.subjectPleiomaltinineen_US
dc.subjectPyroneen_US
dc.subjectThioureaen_US
dc.subjectTotal synthesisen_US
dc.subjectVinylalleneen_US
dc.titleDevelopment of an enantioselective alkaloid addition to pyrones and studies towards the total synthesis of vinylallene natural productsen_US
dc.typeThesis/Dissertation
dc.date.updated2016-02-16T02:16:15Z
etd.degree.nameDoctor of Philosophyen_US
etd.degree.leveldoctoralen_US
etd.degree.disciplineChemistryen_US
etd.degree.grantorBoston Universityen_US


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Attribution 4.0 International
Except where otherwise noted, this item's license is described as Attribution 4.0 International