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Stereodivergent Synthesis of Enantioenriched Five- and Six-Membered Cyclic-1,3-diols and Applications Toward Library Synthesis
dc.contributor.advisor | Aubé, Jeffrey | |
dc.contributor.author | Singh, Gurpreet | |
dc.date.accessioned | 2016-10-11T19:12:43Z | |
dc.date.available | 2016-10-11T19:12:43Z | |
dc.date.issued | 2015-12-31 | |
dc.date.submitted | 2015 | |
dc.identifier.other | http://dissertations.umi.com/ku:14373 | |
dc.identifier.uri | http://hdl.handle.net/1808/21661 | |
dc.description.abstract | Abstract This work describes the development of methods to access synthetically useful chiral diols in enantiomerically pure form. First chapter describes the development of a stereodivergent approach for enantioenriched synthesis of 2-cyclopentene-1,3-diol that was later converted to 4-hydroxy-2-cyclopentenones (4-HCPs), which are highly privileged synthetic building blocks with numerous applications in natural product syntheses and pharmaceuticals. The present approach enables the gram scale synthesis of 4-HCPs with chemically diverse protecting groups, in a stereodivergent manner. In chapter 2, we describe the development of a unified strategy for the stereodivergent synthesis of enantioenriched 1,3-dihydroxy substituted six-membered carbo- and heterocyclic rings. The previously known approaches for accessing these compounds involve multiple synthetic steps and one or more enzymatic steps. We developed a purely synthetic approach to synthesize enantioenriched carbo- and heterocyclic six-membered 1,3-diols from a common, highly economical commercial available starting material. In Chapter 3, we described the development of a small-molecule library of stereochemically diverse compounds by integrating enantioenriched carbo- and heterocyclic 1,3-diols, and natural α-amino acids. | |
dc.format.extent | 228 pages | |
dc.language.iso | en | |
dc.publisher | University of Kansas | |
dc.rights | Copyright held by the author. | |
dc.subject | Organic chemistry | |
dc.subject | Chemistry | |
dc.subject | 3-cyclohexanediols | |
dc.subject | 3-dihydroxypiperidines | |
dc.subject | cyclopentenones | |
dc.subject | piperidines | |
dc.subject | prostaglandin-inspired libraries | |
dc.subject | small-molecule libraries | |
dc.title | Stereodivergent Synthesis of Enantioenriched Five- and Six-Membered Cyclic-1,3-diols and Applications Toward Library Synthesis | |
dc.type | Dissertation | |
dc.contributor.cmtemember | Dutta, Apurba | |
dc.contributor.cmtemember | Aubé, Jeffrey | |
dc.contributor.cmtemember | Rafferty, Michael | |
dc.contributor.cmtemember | Hanson, Paul | |
dc.contributor.cmtemember | Malinakova, Helena | |
dc.thesis.degreeDiscipline | Medicinal Chemistry | |
dc.thesis.degreeLevel | Ph.D. | |
dc.provenance | 04/05/2017: The ETD release form is attached to this record as a license file. | |
dc.rights.accessrights | openAccess |