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dc.contributor.advisorRomo, Daniel
dc.creatorShirley, Morgan
dc.date.accessioned2015-01-09T20:52:31Z
dc.date.available2016-05-01T05:30:59Z
dc.date.created2014-05
dc.date.issued2014-06-06
dc.date.submittedMay 2014
dc.identifier.urihttp://hdl.handle.net/1969.1/152839
dc.description.abstractA history and detailed account of the applications of β-lactones towards natural products and bioactive compounds in the last ten years is discussed as these small heterocycles are becoming more widely recognized for their reactivity, numerous methods of construct, and high degree of functionalization. An improvement to the nucleophile catalyzed aldol-β-lactonization of keto-acids is reported employing commodity reagents delivering gram quantities of bicyclic β-lactone. The first total synthesis of caulolactone A is reported employing a highly diastereoselective biscyclization to a key carvone–derived β-lactone. The natural product was completed from chiral pool (R)-carvone in 10 total steps. Towards rapidly generating complex cyclopentanes an organocatalyzed tandem Michael aldol-lactonization process is reported. Subsequently revealing conditions for an enantioselective variant generating two C-C bonds, one C-O bond, two rings, and up to three contiguous stereocenters from simple starting materials.
dc.format.mimetypeapplication/pdf
dc.language.isoen
dc.subjectNCMAL
dc.subjectBeta-lactones
dc.subjectNCAL
dc.subjectnucleophile catalyzed aldol-lactonization
dc.subjectcaulolactone A
dc.titleβ-Lactones as Key Building Blocks: Synthetic Applications to Diverse Natural Products
dc.typeThesis
thesis.degree.departmentChemistry
thesis.degree.disciplineChemistry
thesis.degree.grantorTexas A & M University
thesis.degree.nameDoctor of Philosophy
thesis.degree.levelDoctoral
dc.contributor.committeeMemberBergbreiter, David E
dc.contributor.committeeMemberYang, Jiong
dc.contributor.committeeMemberBell-Pedersen, Deborah
dc.type.materialtext
dc.date.updated2015-01-09T20:52:32Z
local.embargo.terms2016-05-01
local.etdauthor.orcid0000-0002-8679-4440


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