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Studies toward the total synthesis of microsclerodermin G

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dc.contributor.authorBurnett, Cameron Moeller, author
dc.contributor.authorWilliams, Robert Michael, advisor
dc.contributor.authorKennan, Alan J., committee member
dc.contributor.authorRovis, Tomislav, 1968-, committee member
dc.contributor.authorBernstein, E. R. (Elliot R.), committee member
dc.contributor.authorBelisle, John Theodore, committee member
dc.date.accessioned2007-01-03T05:44:43Z
dc.date.available2007-01-03T05:44:43Z
dc.date.issued2010
dc.descriptionDepartment Head: Ellen R. Fisher.
dc.description.abstractWe report our studies toward the synthesis of microsclerodermin G, a cyclic hexapeptide with antifungal and antitumor activity. The dehydrotryptophan amino acid was synthesized according to literature precedents. (3R)-γ-amino-β-hydroxybutyric acid (GABOB) was synthesized according to previous methodology from our research group. An aspartate-based precursor to the pyrrolidinone moiety of microsclerodermin G was prepared in four steps from known materials. 3-amino-6-methyl-12-phenyl-2,4,5-trihydroxydodeca-7,9,11-trienoic acid (AMPTD) was prepared in seven steps from known materials; the synthesis utilized Evans' chiral oxazolidinone glycolate aldol reaction and the sulfinimine-based Mannich reaction developed by Ellman. Syntheses of two dipeptides are reported, as are other attempts at coupling of the various amino acids.
dc.format.mediumborn digital
dc.format.mediumdoctoral dissertations
dc.identifierBurnett_colostate_0053A_10015.pdf
dc.identifierETDF2010100002CHEM
dc.identifier.urihttp://hdl.handle.net/10217/39035
dc.languageEnglish
dc.language.isoeng
dc.publisherColorado State University. Libraries
dc.relation.ispartof2000-2019
dc.rightsCopyright and other restrictions may apply. User is responsible for compliance with all applicable laws. For information about copyright law, please see https://libguides.colostate.edu/copyright.
dc.subjectsynthesis
dc.subjectAMPTD
dc.subjectmicrosclerodermin G
dc.subjectorganic
dc.subject.lcshMacrocyclic compounds -- Synthesis
dc.subject.lcshPeptides -- Synthesis
dc.subject.lcshAmino acids -- Synthesis
dc.titleStudies toward the total synthesis of microsclerodermin G
dc.typeText
dcterms.rights.dplaThis Item is protected by copyright and/or related rights (https://rightsstatements.org/vocab/InC/1.0/). You are free to use this Item in any way that is permitted by the copyright and related rights legislation that applies to your use. For other uses you need to obtain permission from the rights-holder(s).
thesis.degree.disciplineChemistry
thesis.degree.grantorColorado State University
thesis.degree.levelDoctoral
thesis.degree.nameDoctor of Philosophy (Ph.D.)

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