A novel ene reaction: Development and applications to the synthesis of (+,-)-phyllanthocin

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dc.contributor.advisorCiufolini, Marco A.en_US
dc.creatorDeaton, Melissa Virginiaen_US
dc.date.accessioned2009-06-04T00:34:00Zen_US
dc.date.available2009-06-04T00:34:00Zen_US
dc.date.issued1996en_US
dc.description.abstractA new reaction has been discovered that forms carbon-carbon bonds at room temperature under catalysis by lanthanide reagents. This reaction occurs between vinyl ethers, which have an oxygen functionality located at the central carbon of the allylic system, and aldehydes and is catalyzed by a 1:1 complex of Yb(fod)$\sb3$ and AcOH. The primary product, 3, is not observed but becomes protected, in situ, by excess vinyl ether present as the solvent, or co-solvent, to form the observed product 4. This reaction is very general and proceeds to form pure vinyl ether products in excellent yields. The vinyl ether products formed through the use of this novel reaction can be used to quickly piece together more complex functionalities such as furanones, cyclopentanes, bromoketones, and benzazepinones. Approaches to the efficient syntheses of these compounds and others will be discussed. Phyllanthocin, 5, the aglycon of the potent antitumor agent Phyllanthoside, has been targeted for synthesis using the ene reaction. Furanone formation, using a functionalized vinyl ether formed in the ene reaction, is the primary goal. Applications to the total synthesis of Phyllanthocin will be discussed.$\sp*$ ftn$\sp*$Please refer to the dissertation for diagrams.en_US
dc.format.extent253 p.en_US
dc.format.mimetypeapplication/pdfen_US
dc.identifier.callnoTHESIS CHEM. 1996 DEATONen_US
dc.identifier.citationDeaton, Melissa Virginia. "A novel ene reaction: Development and applications to the synthesis of (+,-)-phyllanthocin." (1996) Diss., Rice University. <a href="https://hdl.handle.net/1911/16922">https://hdl.handle.net/1911/16922</a>.en_US
dc.identifier.urihttps://hdl.handle.net/1911/16922en_US
dc.language.isoengen_US
dc.rightsCopyright is held by the author, unless otherwise indicated. Permission to reuse, publish, or reproduce the work beyond the bounds of fair use or other exemptions to copyright law must be obtained from the copyright holder.en_US
dc.subjectOrganic chemistryen_US
dc.subjectPharmaceutical chemistryen_US
dc.titleA novel ene reaction: Development and applications to the synthesis of (+,-)-phyllanthocinen_US
dc.typeThesisen_US
dc.type.materialTexten_US
thesis.degree.departmentChemistryen_US
thesis.degree.disciplineNatural Sciencesen_US
thesis.degree.grantorRice Universityen_US
thesis.degree.levelDoctoralen_US
thesis.degree.nameDoctor of Philosophyen_US
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