Applications of a novel pyridine-forming reaction: The total syntheses of kuanoniamine D, dercitins, and lavendamycin methyl ester

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dc.contributor.advisorCiufolini, Marco A.en_US
dc.creatorBishop, Michael Josephen_US
dc.date.accessioned2009-06-04T00:02:30Zen_US
dc.date.available2009-06-04T00:02:30Zen_US
dc.date.issued1993en_US
dc.description.abstractSeveral bioactive thiazolopyridoacridines of marine origin have been synthesized. Kuanoniamine D was synthesized in 18 steps from cyclohexanedione mono-ethyleneketal in 7.3% overall yield. The most potent member of the family, dercitin, was also synthesized from cyclohexanedione mono-ethyleneketal in 18 steps and 7.2% overall yield. Nordercitin was produced from the same starting material in 16 steps and 9.3% overall yield. This work also confirms the revision of the controversial structural assignments of dercitin and nordercitin. These efficient total syntheses include a new pyridine-forming sequence and a photochemical nitrene insertion as crucial steps. A novel approach to the streptonigrinoids, a family of potent antitumor antibiotics, is also described. An efficient formal total synthesis of the methyl ester of lavendamycin has been completed to demonstrate the usefulness of this approach. Key steps include a new pyridine-forming sequence and a thermolytic nitrene insertion to form a $\beta$-carboline. This formal synthesis is several steps shorter and an order of magnitude more productive than previously reported synthetic approaches.en_US
dc.format.extent203 p.en_US
dc.format.mimetypeapplication/pdfen_US
dc.identifier.callnoThesis Chem. 1993 Bishopen_US
dc.identifier.citationBishop, Michael Joseph. "Applications of a novel pyridine-forming reaction: The total syntheses of kuanoniamine D, dercitins, and lavendamycin methyl ester." (1993) Diss., Rice University. <a href="https://hdl.handle.net/1911/16599">https://hdl.handle.net/1911/16599</a>.en_US
dc.identifier.urihttps://hdl.handle.net/1911/16599en_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.titleApplications of a novel pyridine-forming reaction: The total syntheses of kuanoniamine D, dercitins, and lavendamycin methyl esteren_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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