Indole alkaloid synthesis

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dc.contributor.advisorWenkert, Ernest
dc.contributor.committeeMemberLewis, Edward S.
dc.contributor.committeeMemberStorck, Roger L.
dc.creatorSimmons, Dana Philip
dc.date.accessioned2018-12-18T21:21:04Z
dc.date.available2018-12-18T21:21:04Z
dc.date.issued1983
dc.description.abstractIndole acetic acid and methyl 1,4,5,6-tetrahydronicotinylacetate obtained by hydrogenation of methyl nicotinylacetate were combined in the presence of base to yield methyl 1-(3-indoleacetyl)-1,4,5,6-tetrahydronicotinylacetate in 45% yield. This, upon heating in polyphosphoric acid, yielded in 73% 2-deethyl-5,17-diketo-2,16-dihydrovincadifformine with complete stereospecific formation of all five chiral centers. Reduction of the two keto functions led to 2-deethyl-2,16-dihydrovincadifformine, whereas reduction of the lactam and oxidation of the 2,16 carbon-carbon bond yielded 2-deethyl-16-ketovincadifformine. 16 ketopseudovincadifformine was prepared in the same manner starting from methyl 5-ethyl-nicotinylacetate.
dc.format.digitalOriginreformatted digital
dc.format.extent77 pp
dc.identifier.callnoThesis Chem. 1983 Simmons
dc.identifier.citationSimmons, Dana Philip. "Indole alkaloid synthesis." (1983) Diss., Rice University. <a href="https://hdl.handle.net/1911/104330">https://hdl.handle.net/1911/104330</a>.
dc.identifier.digitalRICE1962
dc.identifier.urihttps://hdl.handle.net/1911/104330
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.titleIndole alkaloid 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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