A novel tin-mediated indole synthesis and its application to natural product synthesis

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dc.contributor.advisorFukuyama, Tohru
dc.creatorPeng, Ge
dc.date.accessioned2009-06-04T00:35:36Z
dc.date.available2009-06-04T00:35:36Z
dc.date.issued1996
dc.description.abstractA new indole synthesis is described. The key step involves a novel tin-mediated free radical reaction to generate unstable 2-tri-n-butylstannyl-3-substituted indoles, which upon mild acidic workup, furnishes 3-substituted indoles. The 2-tri-n-butylstannyl-3-substituted indoles are also subjected to a one-pot Stille coupling to provide 2,3-disubstituted indoles. Two applications of the above methodology are also described. The efficient total synthesis of (${\pm})$-vincadifformine involves the construction of the indole skeleton by using this indole formation reaction and a novel amine protection-deprotection procedure as crucial steps. A new synthetic approach is explored towards the total synthesis of antitumor agent discorhabdin C. The key step towards the key intermediate has greatly contributed to the development of the novel indole synthesis methodology.
dc.format.extent178 p.en_US
dc.format.mimetypeapplication/pdf
dc.identifier.callnoThesis Chem. 1996 Peng
dc.identifier.citationPeng, Ge. "A novel tin-mediated indole synthesis and its application to natural product synthesis." (1996) Diss., Rice University. <a href="https://hdl.handle.net/1911/16930">https://hdl.handle.net/1911/16930</a>.
dc.identifier.urihttps://hdl.handle.net/1911/16930
dc.language.isoeng
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.
dc.subjectOrganic chemistry
dc.subjectPharmaceutical chemistry
dc.titleA novel tin-mediated indole synthesis and its application to natural product synthesis
dc.typeThesis
dc.type.materialText
thesis.degree.departmentChemistry
thesis.degree.disciplineNatural Sciences
thesis.degree.grantorRice University
thesis.degree.levelDoctoral
thesis.degree.nameDoctor of Philosophy
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