Application of a novel carbonyl ene reaction: Total syntheses of phyllanthocin and chlorovulone II

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dc.contributor.advisorCiufolini, Marco A.en_US
dc.creatorZhu, Shurenen_US
dc.date.accessioned2009-06-04T08:48:16Zen_US
dc.date.available2009-06-04T08:48:16Zen_US
dc.date.issued1998en_US
dc.description.abstractWe describe the total syntheses of $(\pm)$-phyllanthocin (1), the aglycon of the potent antineoplastic agent phyllanthoside (2a), and of $(\pm)$-chlorovulone II (3), a halogenated marine prostanoid with high antiproliferative and cytotoxic activity.* The key step of both syntheses is a novel carbonyl ene reaction, which occurs between ordinary aldehydes and vinyl ethers that display the oxygen functionality at the central carbon of an allylic system, e.g., 2-methoxypropene, under the catalytic influence of 0.5 mol% of the 1:1 complex of Yb(fod)$\sb3$ and acetic acid (Figure I).* ftn*Please refer to dissertation for diagrams.en_US
dc.format.extent163 p.en_US
dc.format.mimetypeapplication/pdfen_US
dc.identifier.callnoTHESIS CHEM. 1998 ZHUen_US
dc.identifier.citationZhu, Shuren. "Application of a novel carbonyl ene reaction: Total syntheses of phyllanthocin and chlorovulone II." (1998) Diss., Rice University. <a href="https://hdl.handle.net/1911/19334">https://hdl.handle.net/1911/19334</a>.en_US
dc.identifier.urihttps://hdl.handle.net/1911/19334en_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 sciencesen_US
dc.titleApplication of a novel carbonyl ene reaction: Total syntheses of phyllanthocin and chlorovulone IIen_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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