Thesis (M.S.)--Boise State University, 2009. / Includes bibliographical references (leaves 89-94).

Thesis (M.S.)--Boise State University, 2009. / Title from t.p. of PDF file (viewed Apr. 9, 2010). Includes abstract. Includes bibliographical references (leaves 89-94).

Reproduction de : Thèse doctorat : Pharmacie. Biologie cellulaire et moléculaire : Reims : 2007. / Titre provenant de l'écran-titre. Bibliographie f.118-130.

Thesis (Ph. D.)--University of Texas at Austin, 2007. / Vita. Includes bibliographical references.

No description available.

No description available.

No description available.

No description available.

A general and efficient methodology for the synthesis of cis-2-substituted-1,2-dihydro-1-naphthols and 2-substituted-1-naphthols from oxabenzonorbornadienes was developed. The procedure involved the sequential palladium-catalyzed ring opening of oxabenzonorbornadienes with aryl or vinyl halides followed by oxidation of the intermediate dihydronaphthols with IBX. The scope of the palladium-catalyzed coupling was extended to a variety of halides such as aryl iodides and bromides bearing both electron-withdrawing and -donating groups, vinyl bromides, and glycal iodides. Oxidation of cis-2-substituted-1,2-dihydro-1-naphthols using IBX led to 2-substituted-1-naphthols in good to excellent yields. Application of such methodologies successfully led to a Group II C-aryl glycoside model. The double intramolecular benzyne-furan cycloadditions and naphthyne-furan cycloadditions were developed. In the model studies, furans and the reacting benzynes or naphthynes were linked with silicon tethers and, thus, the regiochemistry of Diels-Alder cycloadditions could be controlled. Two different tactics for converting the resultant oxabenzonorbornadienes to substituted anthrarufins were demonstrated. The first method entails the initial cleavage of the silicon tethers followed by regioselective ring opening of the oxabenzonorbornadienes and oxidation of the central ring giving the target anthrarufin, whereas the second features the regioselective ring opening of the oxabenzonorbornadienes followed by protiodesilylation and oxidation. Application of the chemistry demonstrated in the model double benzyne-furan cycloadditions successfully led to a total synthesis of vineomycinone B2 methyl ester. This strategy enables the rapid assembly of the glycosyl-substituted aromatic frameworks of complex C-aryl glycoside antibiotics from simple starting materials. We propose an oxidative Mannich reaction for the synthesis of an indole natural product, actinophyllic acid. The synthesis features the selective oxidation of a C3-alkyl indole followed by intramolecular nucleophilic addition of enol ether to build a bicylcic framework. This approach may provide a convergent access to the skeleton of actinophyllic acid. Currently, we have prepared indole 5.77, and continuing efforts will be focused on the formation of azepino[4,3-b]indole 5.78 and the key oxidative Mannich reaction. / text

Several strategies outlining approaches to the synthesis of the heteroanthracyclinones 4-demethoxyxanthodaunomycinone and 4-demethoxyisoxanthodaunomycinone (7,8,9,10-tetrahydrobenzo(b)-6,7,9,11-tetrahydroxy-9-acetylxanthen-12 and 5-one) are described. / The condensation of tetralin 2-acetyl-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthol with o-methoxybenzoic acid was investigated and useful large-scale syntheses of important 1,4-dimethoxy-substituted xanthone intermediates were developed. / Diels-Alder cycloaddition reaction between a xanthone-derived o-quinodimethane intermediate and an olefin afforded a low yield of adduct. On the other hand, excellent yields of isolable but labile adducts were obtained in the cycloaddition reaction between xanthoquinone (and also thioxanthoquinone) and Danishefsky's dienes. The formation of linear vs internal adducts was rationalized on the grounds of resonance and FMO theory. Efforts to induce unactivated dienes to cycloadd using catalysts as well as annulation studies on model compounds using the novel reagent (E)-N-vinylpyrrolidine-(beta)-(2-lithio-1,3-dithian-2-yl) (as a synthon of the (alpha),(beta)-dianion of acetaldehyde) are discussed. / The synthesis of daunomycin and xanthodaunomycin analogs carrying a carbon substituent at position 7 were not accessible using the Diels-Alder cycloaddition reaction as diene 1-carbomethoxy-3-triethylsilyloxy-1,3-butadiene failed to react with either quinizarinquinone or xanthoquinone even at elevated temperatures. / The compound 4-hydroxy-1- 2- (2-hydroxyethyl)amino ethyl amino xanthone and the 4-methoxy derivative were prepared and found to be inactive in the in vivo P-388 mouse leukemia model system.