A stereocontrolled total synthesis of (+,-)-renieramycin A

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dc.contributor.advisorFukuyama, Tohru
dc.creatorLinton, Steven Douglas
dc.date.accessioned2009-06-04T00:39:28Z
dc.date.available2009-06-04T00:39:28Z
dc.date.issued1992
dc.description.abstractA novel synthetic route via iterative condensations of piperazinedione and substituted benzaldehydes has resulted in the first total synthesis of the complex antibiotic, renieramycin A 1a. Salient features include an acyliminium ion-mediated construction of a diazabicyclo (3.3.1) nonane nucleus, which allows for stereoselective hydrogenation and benzylic oxidation. The stereochemistry of the angelate side chain was unequivocally determined by X-ray crystallographic analysis of the penultimate intermediate, 67b. (DIAGRAM, TABLE OR GRAPHIC OMITTED...PLEASE SEE DAI)
dc.format.extent149 p.en_US
dc.format.mimetypeapplication/pdf
dc.identifier.callnoThesis Chem. 1992 Linton
dc.identifier.citationLinton, Steven Douglas. "A stereocontrolled total synthesis of (+,-)-renieramycin A." (1992) Diss., Rice University. <a href="https://hdl.handle.net/1911/16531">https://hdl.handle.net/1911/16531</a>.
dc.identifier.urihttps://hdl.handle.net/1911/16531
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 stereocontrolled total synthesis of (+,-)-renieramycin A
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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