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dc.contributor.advisorAndrade, Rodrigo B.
dc.creatorZhao, Senzhi
dc.date.accessioned2020-11-05T19:50:47Z
dc.date.available2020-11-05T19:50:47Z
dc.date.issued2015
dc.identifier.other958157185
dc.identifier.urihttp://hdl.handle.net/20.500.12613/4093
dc.description.abstractAll Strychnos and Aspidosperma alkaloids possess a core pyrrolo[2,3-d]carbazole ABCE tetracycle. In order to develop an efficient and divergent methodology for the synthesis of Strychnos alkaloids, a streamlined synthetic sequence to the ABCE tetracycle has been developed. It features a Mitsunobu activation of an N-hydroxyethyl gramine intermediate and subsequent intramolecular aza-Baylis-Hillman reaction. This method was first applied in the total synthesis of (±)-alstolucine B. Additional key steps in the synthesis included (1) chemoselective intermolecular and intramolecular Michael additions and (2) a Swern indoline oxidation. The second application of this method was in the first total synthesis of (-)-melotenine A, a novel rearranged Aspidosperma alkaloid with potent biological activity. Additional key steps in the synthesis included (1) a Piers annulation of a vinyl iodide and a methyl ketone to prepare the D ring and (2) a site-selective intermolecular vinylogous aldol reaction
dc.format.extent363 pages
dc.language.isoeng
dc.publisherTemple University. Libraries
dc.relation.ispartofTheses and Dissertations
dc.rightsIN COPYRIGHT- This Rights Statement can be used for an Item that is in copyright. Using this statement implies that the organization making this Item available has determined that the Item is in copyright and either is the rights-holder, has obtained permission from the rights-holder(s) to make their Work(s) available, or makes the Item available under an exception or limitation to copyright (including Fair Use) that entitles it to make the Item available.
dc.rights.urihttp://rightsstatements.org/vocab/InC/1.0/
dc.subjectChemistry
dc.subjectChemistry, Organic
dc.subjectAspidosperma Alkaloids and Bis-aspidosperma Alkaloids
dc.subjectMelotenine A
dc.subjectMethodology Development
dc.subjectStrychnos Alkaloids and Bis-strychnos Alkaloids
dc.subjectSungucine
dc.subjectTotal Synthesis of Natural Products
dc.titleNOVEL APPROACHES TO STRYCHNOS AND ASPIDOSPERMA ALKALOIDS
dc.typeText
dc.type.genreThesis/Dissertation
dc.contributor.committeememberAndrade, Rodrigo B.
dc.contributor.committeememberDavis, Franklin A.
dc.contributor.committeememberSieburth, Scott McNeill
dc.contributor.committeememberCannon, Kevin C.
dc.description.departmentChemistry
dc.relation.doihttp://dx.doi.org/10.34944/dspace/4075
dc.ada.noteFor Americans with Disabilities Act (ADA) accommodation, including help with reading this content, please contact scholarshare@temple.edu
dc.description.degreePh.D.
refterms.dateFOA2020-11-05T19:50:47Z


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