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Thesis (Ph. D.)--University of Texas at Austin, 2000. / Vita. Includes bibliographical references (leaves 263-272). Available also in a digital version from Dissertation Abstracts.

Thesis (Ph. D.)--University of Texas at Austin, 1999. / Vita. Includes bibliographical references (leaves 234-250). Available also in a digital version from Dissertation Abstracts.

Thesis (Ph. D.)--University of Texas at Austin, 2005. / Vita. Includes bibliographical references.

Thesis (Ph. D.)--University of Texas at Austin, 2005. / Vita. Includes bibliographical references.

The synthesis of several 6-Chlorodemethyllavendamycin analogs and their chemistry are described. In this investigation the following compounds were prepared:6-Chlorodemethyllavendamycin methyl ester, 6-Chlorodemethyllavendamycin ethylester, 6-Chlorodemethyllavendamycin butyl ester, 6-Chlorodemethyllavendamycin isoamyl ester, 6-Chlorodemethyllavendamycin octyl ester, and 6-Chlorodemethyllavendamycin amide. Pictet Spengler condensation of 7-amino-6-chloro-2-formylquinoline-5,8-dione with tryptophan methyl ester, tryptophan ethyl ester, tryptophan butyl ester, tryptophan isoamyl ester, tryptophan octyl ester, and tryptophan amide in anisole afforded the compounds. 7-amino-6-chloro-2-formylquinoline-5,8-dione was prepared according to the following general procedures.The first step is the nitration of 8-Hydroxy-2-methylquinoline. 8-Hydroxy-2methylquinoline is reacted with 70% mixture of HNO3/H2SO4 to produce 5,7-dinitro-8hydroxy-2-methylquinoline. The next step requires hydrogenation and acylation. 5,7Dinitro-8-hydroxy-2-methylquinoline was reduced by H2/Pd-C in the presence of HCl and H20 filtered and then treated with sodium sulfite, sodium acetate and acetic anhydride to yield 5,7-diacetamido-8-acetoxy-2-methylquinoline. 5,7-Diacetamido-8-acetoxy-2methylquinoline was oxidized by potassium dichromate to produce 7-acetamido-2methylquinoline-5,8-dione. 7-Acetamido-2-methylquinoline-5,8-dione was chlorinated using hydrogen chloride gas in dry methanol producing 7-amino-6-chloro-2methylquinoline-5,8-dione. Treatment of 7-amino-6-chloro-2-methylquinoline-5,8-dione with selenium dioxide, under reflux in 1,4-dioxane produced 7-amino-6-chloro-2formylquinoline-5, 8-dione.All structures were confirmed by 'H NMR, IR, EIMS, and HRMS. / Department of Chemistry

Thesis (Ph. D.)--University of Texas at Austin, 2002. / Vita. Includes bibliographical references. Available also from UMI Company.

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The synthesis of 7-N-acetyldemethyllavendamycin butyl amide (47), 7-Nacetyldemethyllavendamycin isopropyl amide (48), 7-N-acetyldemethyllavendamycin amide of piperidine (49), 7-N-acetyldemethyllavendamycin amide of pyrrolidine (50), 7N-acetyldemethyllavendamycin amide of morpholine (51), demethyllavendamycin butyl amide (52), demethyllavendamycin amide of pyrrolidine (53), and demethyllavendamycin amide of morpholine (54) are described. Pictet Spengler condesation of 7-acetamido-2formylquinoline-5,8-dione (28) with tryptophan butyl amide (66), tryptophan isopropyl amide (67), tryptophan amide of piperidine (68), tryptophan amide of pyrrolidine (69), and tryptophan amide of morpholine (70) in an anisole - pyridine solution directly afforded the five lavendamycin amides 47-51. Compounds 52, 53, and 54 were obtained by hydrolysis of 47, 50, and 51 with 70% H2SO4-H20 solution.Aldehyde 28 was prepared according to the following general procedure.Nitration of 8-hydroxy-2-methylquinoline (30) yielded 8-hydroxy-2-methyl-5,7 dinitroquinoline (31). Compound 31 was then hydrogenated and acylated with acetic anhydride to yield 5,7-diacetamido-2-methyl-8-acetoxyquinoline (33). Compound 33 was oxidized by potassium dichromate to give 7-acetamido-2-methylquinoline-5,8-dione (27). Treatment of 27 with selenium dioxide in refluxing 1,4-dioxane afforded compound 28.Compounds 66, 67, 68, 69, and 70 were synthesized from compounds 61,62, 63, 64, and 65. These compounds were deprotected with ammonium formate in the presence of 10% Palladium on charcoal in methanol under an argon balloon at atmospheric pressure.Compounds 61, 62, 63, 64, and 65 were obtained from 58 with butylamine, isopropylamine, piperidine, pyrrolidine, and morpholine respectively in the presence of triethylamine under an argon balloon at atmospheric pressure.Compound 58 was synthesized by the reaction of N-carbobenzyloxytryptophan, with N-hydroxy succinimide, in the presence of N-dicyclohexylcarbodimide in dried and distilled dioxane under an argon balloon at atmospheric pressure.The structures of the novel compounds 58, 47, 48, 49, 50, 51, 52, 53, and 54 were confirmed by 1H NMR, IR, EIMS, and HRMS.The structures of protected and deprotected amides 61, 62, 63, 64, 65, 66, 67, 68, 69, and 70 were also confirmed by 1 H NMR and IR spectroscopy. / Department of Chemistry