New approaches to total synthesis of quinoid antitumor agents: Cystodytins and discorhabdins

Simple item page
dc.contributor.advisorCiufolini, Marco A.en_US
dc.creatorByrne, Norman Edwarden_US
dc.date.accessioned2009-06-04T00:42:15Zen_US
dc.date.available2009-06-04T00:42:15Zen_US
dc.date.issued1991en_US
dc.description.abstractA new pyridine synthesis is described. The key step involves a modified Knoevenagel-Stobbe reaction in which the treatment of an alkoxy-dihydropyran with hydroxylamine hydrochloride generates highly substituted pyridine ring systems. Approaches to efficient syntheses of important natural products in including aza-analogs of polynuclear aromatic hydrocarbons, Eupolauramine, and Streptonigrin are explored. Antitumor agents Cystodytin A and B were synthesized in 13 steps from 4-hydroxyethyl cyclohexanone in an overall yield of 7%. This efficient total synthesis involves the new pyridine reaction and a photochemical nitrene insertion as crucial steps. Various approaches are explored toward the total synthesis of antitumor agent Discorhabdin C. The first synthetically useful Paterno-Buchi reaction between benzoquinone and an olefin was discovered. Various applications of this reaction are described, including its use for the synthesis of Discorhabdin C.en_US
dc.format.extent449 p.en_US
dc.format.mimetypeapplication/pdfen_US
dc.identifier.callnoThesis Chem. 1991 Byrneen_US
dc.identifier.citationByrne, Norman Edward. "New approaches to total synthesis of quinoid antitumor agents: Cystodytins and discorhabdins." (1991) Diss., Rice University. <a href="https://hdl.handle.net/1911/16424">https://hdl.handle.net/1911/16424</a>.en_US
dc.identifier.urihttps://hdl.handle.net/1911/16424en_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.titleNew approaches to total synthesis of quinoid antitumor agents: Cystodytins and discorhabdinsen_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
Files
Original bundle
Now showing 1 - 1 of 1
Thumbnail Image
Name:
9136004.PDF
Size:
6.55 MB
Format:
Adobe Portable Document Format
Download
Collections
Rice University Theses and Dissertations