The Total Synthesis of () 7-HDHA

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dc.contributor.advisorOrellana Garcia, Josue Arturo
dc.contributor.authorZhang, Minhao
dc.date.accessioned2020-05-11T12:42:19Z
dc.date.available2020-05-11T12:42:19Z
dc.date.copyright2019-09
dc.date.issued2020-05-11
dc.date.updated2020-05-11T12:42:18Z
dc.degree.disciplineChemistry
dc.degree.levelMaster's
dc.degree.nameMSc - Master of Science
dc.description.abstractFatty acid () 7-HDHA was recently identified as an endogenous ligand for PPAR/ receptors by one of our collaborators Dr. Henry Krause group. While this discovery is promising in understanding PPARs mechanism of effects and related diseases (Alzheimers disease, cerebral ischemia, retina inflammation, etc.), the study of 7-HDHA in relation to PPARs has been hampered by the high cost and limited supply of 7-HDHA. The total synthesis of 7-HDHA was attempted using four different strategies, and finally achieved in 11 steps in the longest reaction sequence, starting from commercially available (triisopropylsilyl)acetylene and 2-pentyn-1-ol. The overall yield of this synthesis was 12%. This concise route mainly relies on the one-step generation of three Z-double bonds with the semi-hydrogenation catalyst P2-Nickel, and a late-stage semi-hydrogenation with Zn(Cu/Ag) reagent. The completion of this synthesis will now provide large quantities of 7-HDHA quickly, and thus enable extensive studies of PPAR 7-HDHA interaction.
dc.identifier.urihttps://hdl.handle.net/10315/37385
dc.languageen
dc.rightsAuthor owns copyright, except where explicitly noted. Please contact the author directly with licensing requests.
dc.subjectMolecular chemistry
dc.subject.keywords7-HDHA
dc.subject.keywordsFatty acid
dc.subject.keywordsTotal synthesis
dc.subject.keywordsppar
dc.subject.keywordsP2-Nickel
dc.subject.keywordsNatural product
dc.subject.keywordsrcm
dc.subject.keywordsRing-closing metathesis
dc.subject.keywordsHydroxyl docosahexaenoic acid
dc.subject.keywordsSemi-hydrogenation
dc.subject.keywordsSonogashira
dc.subject.keywordsClaisen rearrangement
dc.titleThe Total Synthesis of () 7-HDHA
dc.typeElectronic Thesis or Dissertation

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