DIASTEREOSELECTIVE 1,4-CONJUGATE ADDITION TO -SUBSTITUTED ENONES AND PROGRESS TOWARD THE TOTAL SYNTHESIS OF BRAZILIDE A

dc.contributor.advisorMay, Jeremy A.
dc.contributor.committeeMemberDaugulis, Olafs
dc.contributor.committeeMemberFaler, Catherine A.
dc.contributor.committeeMemberTeets, Thomas S.
dc.contributor.committeeMemberHarth, Eva M.
dc.creatorPlasko, Davis Phillips
dc.date.accessioned2021-08-04T02:16:33Z
dc.date.createdAugust 2020
dc.date.issued2020-08
dc.date.submittedAugust 2020
dc.date.updated2021-08-04T02:16:35Z
dc.description.abstractAn organocatalytic enantioselective 1,4-conjugate addition to enones that controls the absolute stereoselectivity of the chiral center generated at the -position of the carbonyl has been developed. The inclusion of -substituents in the enone adds a new chiral center, and a diastereomeric relationship, in the product as shown in Scheme 1. Therefore, it is desired to be able to control the diastereoselectivity of the product, leading to the formation of two chiral centers that are independently controlled in one step via an enantioselective protonation of the transient boron enolate. Brazilide A has been isolated from Sappan lignum, a traditional Chinese medicine. Only one total synthesis of brazilide A has been published due to the complexity of the propellane core. A rhodium carbene-cascade, followed with a base-catalyzed rearrangement, developed by the May lab, forms the propellane core as shown in Scheme 2. This methodology allows for a concise, and high-yielding formation of the structurally complex propellane core that will allow for a novel synthesis of brazilide A.
dc.description.departmentChemistry, Department of
dc.format.digitalOriginborn digital
dc.format.mimetypeapplication/pdf
dc.identifier.urihttps://hdl.handle.net/10657/7976
dc.language.isoeng
dc.rightsThe author of this work is the copyright owner. UH Libraries and the Texas Digital Library have their permission to store and provide access to this work. Further transmission, reproduction, or presentation of this work is prohibited except with permission of the author(s).
dc.subjectorganic chemistry
dc.titleDIASTEREOSELECTIVE 1,4-CONJUGATE ADDITION TO -SUBSTITUTED ENONES AND PROGRESS TOWARD THE TOTAL SYNTHESIS OF BRAZILIDE A
dc.type.dcmiText
dc.type.genreThesis
local.embargo.lift2022-08-01
local.embargo.terms2022-08-01
thesis.degree.collegeCollege of Natural Sciences and Mathematics
thesis.degree.departmentChemistry, Department of
thesis.degree.disciplineChemistry
thesis.degree.grantorUniversity of Houston
thesis.degree.levelMasters
thesis.degree.nameMaster of Science

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