Dissertations / Theses on the topic 'Indolizidine'
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Nelson, A. "Synthesis of bioactive indolizidine alkaloids." Thesis, Queen's University Belfast, 2005. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.421009.
Full textPadmanabhan, Padma. "Biosynthetic studies on the indolizidine alkaloid cyclizidine." Thesis, University of Cambridge, 1989. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.304387.
Full textMitchell, Douglas. "Synthetic studies towards pyrrolizidine and indolizidine alkaloids." Thesis, Sheffield Hallam University, 1992. http://shura.shu.ac.uk/20067/.
Full textSt-Denis, Yves. "Studies toward the synthesis of hydroxylated indolizidine alkaloids." Thesis, McGill University, 1991. http://digitool.Library.McGill.CA:80/R/?func=dbin-jump-full&object_id=70343.
Full textSecondly, the intramolecular nucleophilic cyclisation of free amines bearing suitable leaving groups was attempted, providing an easy method for the formation of the indolizidine system, with an interesting entry into the synthesis of biologically active polyhydroxylated alkaloids Swainsonine and Castanospermine. The synthesis of these two natural compounds, as well as some of their analogues, using the successful nucleophilic methodology was attempted.
Finally, the regioselective and stereoselective introduction of hydroxyl groups into the pyrrolidine ring system was studied in order to prepare mono- and di-hydroxylated pyrrolidines for the synthesis of the aforementioned natural products.
Kefalas, Panagiotis. "Synthèse d'une indolizidine hydroxylée, analogue de la castanospermine." Paris 11, 1988. http://www.theses.fr/1988PA112340.
Full textSeveral attempts for the synthesis of the indolizidinic alkaloid (1S,6S,7R,8R,8aR)-1,6,7,8 tetrahydroxy-octahydroindolizine (castanospermine), a glucosidase inhibitor and of its epimers are described. The general synthetic approach was undertaken starting from sugars that have an established configuration on the carbon atoms corresponding to the C-6, C-7 and C-8 centres of the indolizidinic ring. Ln a first synthetic route we have studied the formation of the alkaloid five-member ring, through the application of α-aminonitrile chemistry on the aldehyde 1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose prepared from D-(+)-Glucose; either by formation of the N-benzyl,α-aminonitrile, followed by the introduction of C-2 and C-3 and cyclization, or by the synthesis of the α-aminonitrile carrying C-2 and C-3 substituted on the amine function and ring closure. The difficulties met during this route obliged us to abandon. In a second approach we have studied the formation of the polyhydroxylated indolizidinic ring starting from D-Glucose, D-Xylose and D-Arabinose derivatives; we introduce C-1, C-2 and C-3 and the oxygen on C-1 in the form of an enol ether, by Wittig reaction. Then we form a 1,2-oxazine-3,6- dihydro-2H; 4 ethoxy by Diels-Alder reaction with a dienophile carrying the nitroso function. The glucose derivative does not meet the requirements for the continuation of the synthesis, due to the sensitivity of the furan ring in the basic medium of the Wittig reaction. Cyclization of the oxazine on the tosylated sugar frame supplies a bicyclic product. Reduction of the double bond and the N-O bond of the arabinose series derivative give a δ-aminoalcohol which leads to the (1S,6S,7R,8R,8aS),1-ethoxy,6-hydroxy;7,8-O- isopropylidene octahydroindolizine(ie. A close analog of castanospermine) by dehydrative cyclization. (Mitsunobu reaction). The same reaction sequence could not be used on the bicyclic xylose derivative; the Mitsunobu reaction being inappropriate for steric reasons
Agarwal, Sameer. "Transition Metal-Mediated Syntheses of Yohimbane and Indolizidine Alkaloids." Doctoral thesis, Saechsische Landesbibliothek- Staats- und Universitaetsbibliothek Dresden, 2005. http://nbn-resolving.de/urn:nbn:de:swb:14-1119360417222-39155.
Full textKondakal, Vishnu. "The attempted synthesis of indolizidine and pyrrolizidine natural products." Thesis, University of Huddersfield, 2013. http://eprints.hud.ac.uk/id/eprint/19281/.
Full textSzeto, Peter. "Recent development in indolizidine alkaloids : a synthesis of (-)-slaframine." Thesis, University of Bristol, 1995. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.294850.
Full textKefalas, Panagiotis. "Synthèse asymétrique d'une indolizidine hydroxylée, analogue de la castanospermine." Grenoble 2 : ANRT, 1988. http://catalogue.bnf.fr/ark:/12148/cb37614731r.
Full textFarrant, Elizabeth. "A novel approach to the synthesis of polyhydroxylated indolizidine alkaloids." Thesis, University of Reading, 1997. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.360718.
Full textCuthbertson, James D. "New routes to indolizidine alkaloids : the total synthesis of (-)-grandisine B." Thesis, University of York, 2011. http://etheses.whiterose.ac.uk/1970/.
Full textFox, Martin Edward. "Intramolecular cycloaddition reactions of nitrones and hydroxylamines." Thesis, University of Cambridge, 1992. https://www.repository.cam.ac.uk/handle/1810/272243.
Full textSantarem, Marco. "Synthèse diastéréosélective d’alcaloïdes tricycliques : la (+)-géphyrotoxine et les myrmicarines (-) 217, (+)-215A et (-)-215B." Paris 6, 2010. http://www.theses.fr/2010PA066738.
Full textTumidajski, Stephanie. "[4 + 2] cycloadditions of iminoacetonitriles : synthesis of highly substituted tetrahydropyridines and indolizidine alkaloids." Thesis, Massachusetts Institute of Technology, 2013. http://hdl.handle.net/1721.1/84378.
Full textCataloged from PDF version of thesis.
Includes bibliographical references.
Iminoacetonitriles participate as activated imino dienophiles in intermolecular and intramolecular aza Diels-Alder reactions affording tetrahydropyridines and indolizidines. The [alpha]-amino nitrile cycloadducts are versatile synthetic intermediates that participate in a variety of stereoselective transformations to further elaborate the six-membered ring. This thesis describes the scope of the intermolecular [4 + 2] cycloaddition of N-benzyliminoacetonitrile with unactivated and activated dienes, as well as, the synthetic elaboration of the cycloadducts. This thesis also describes the worked performed to complete the total syntheses of indolizidines (-)- 235B', (-)-235B", and (+)-235B" using the aza Diels-Alder reaction of an iminoacetonitrile as the key step.
by Stephanie Tumidajski.
Ph.D.
Lu, Yuanyuan. "Indolizidine and quinolizidine motifs for the synthesis of conformationally constrained smac mimetics and chloroquine conjugates." Doctoral thesis, Universitat Autònoma de Barcelona, 2014. http://hdl.handle.net/10803/283725.
Full textThe indolizidine and quinolizidine framework is present in many natural and synthetic compounds, some of which display diverse bioactivities. This thesis focuses on the stereoselective preparation of chiral indolizidine and quinolizidine derivatives with a double purpose: i) as precursors of conformationally constrained Smac peptidomimetics and ii) to form conjugates with chloroquine residues, in the search for new antimalarial drugs against resistant strains. For the first purpose, it has been applied an approach previously developed in our group for the stereocontrolled synthesis of N-substituted indolizidines and quinolizidines. The first key step of the sequence is the palladium-catalyzed enantioselective allylation of succinimide and glutarimide with racemic butadiene monoxide, wherein the absolute configuration of the allylated products is controlled by the sense of chirality of the palladium ligand. The next steps to the fused azabicyclic compounds included regioselective reduction of the imide, followed by nucleophilic allylation and then ring closing metathesis (RCM). In the event, the configurations of the intermediates and products were established by X-ray diffraction analysis. This strategy was later on extended to α-amino succinimide and glutarimide substrates. The new sequence for the indolizidine derivatives started from L-aspartic acid, which was converted into a protected (3S)-3-amino-2,5-pyrrolidinedione in a few steps. The asymmetric allylation worked well on this substrate, providing a unique stereoisomer. The key regioselective reduction was achieved by using DIBAL-H, and the subsequent nucleophilic allylation and RCM furnished the expected α-aminoindolizidine as a balanced mixture of two epimers. Their relative and absolute configuration was inferred from NMR experiments, including COSY and NOESY spectra. The conversion of these intermediates into the targeted indolizidine peptidomimetics is currently in progress. For the α-aminoquinolizidine analogs, a parallel sequence starting from L-glutamic acid was explored. Unfortunately, in this case the asymmetric allylation did not furnish the expected product and the replacement of the palladium ligand by PPh3 showed limited assistance. Several attempts with a different nitrogen protection were also negative and will be re-examined in the future. For the second purpose, two alternative approaches were considered depending of the nucleophilic or electrophilic character of each reaction partner. With this aim, several nucleophilic and electrophilic azabicycles and chloroquine derivatives were prepared. Unluckily, in the different reactions explored up to now, the expected conjugate was never detected.
Katavic, Peter L., and n/a. "Chemical Investigations of the Alkaloids from the Plants of the Family Elaeocarpaceae." Griffith University. School of Science, 2006. http://www4.gu.edu.au:8080/adt-root/public/adt-QGU20070710.160928.
Full textFellah, Mouloud. "Synthèses diastéréosélectives de l’indolizidine (+)-223A, de la (-)-lasubine II et de la quinolizidine (-)-217A." Paris 6, 2009. http://www.theses.fr/2010PA066034.
Full textKatavic, Peter L. "Chemical Investigations of the Alkaloids from the Plants of the Family Elaeocarpaceae." Thesis, Griffith University, 2006. http://hdl.handle.net/10072/367380.
Full textThesis (PhD Doctorate)
Doctor of Philosophy (PhD)
School of Science
Full Text
Bur, Scott Kenneth. "Studies on the vinylogous Mannich reaction and its application to the synthesis of indolizidine natural products /." Digital version:, 2000. http://wwwlib.umi.com/cr/utexas/fullcit?p9992758.
Full textKawamura, Meire Yasuko. "Emprego de diazocetonas α,β-insaturadas com geometria Z na direta construção de esqueletos indolizidínicos e piperidínicos funcionalizados." Universidade de São Paulo, 2016. http://www.teses.usp.br/teses/disponiveis/75/75133/tde-26082016-104019/.
Full textPumiliotoxins and their congeners are a class of compounds isolated from the skin of some frogs from the Dendrobatidae, Mantellidae, Bufonidae, e Myobatrachidae families, possessing interesting pharmacological activities (cardiotonic activity in low concentrations). Because of the big number of compounds among these toxins (about 100), synthetic methodologies that provide the preparation of these compounds (as well as analogues) in great amounts and in a fast and efficient way using common intermediates, are very important for application in chemical-biology. The α,β-unsaturated diazoketones are promising intermediates for the rapid and efficient synthesis of a range of chemical skeletons, among them, the construction of indolizidine skeleton that pumiliotoxins present. It is important to note that α,β-unsaturated diazoketones with Z geometry (prepared from amino aldehydes) have already the correct stereochemistry for a direct cyclization to construct indolizidine skeletons. The key steps of the work consisted in the preparation of N-protected amino aldehydes, evaluation of Horner-Wadsworth-Emmons reaction in order to obtain α,β-unsaturated diazoketones with Z geometry, and the intramolecular N-H insertion reaction to provide the indolizidine cycle. Another part of the work consisted in the synthesis of iminosugars with piperidine core and aliphatic side chains (application in medicinal chemistry) and in the synthesis of (-)-1-deoxy-altronojirimycin, applying the same methodology (use of α,β-unsaturated diazoketones with Z geometry).
Bertonha, Ariane Fernandes. "Construção do esqueleto 6-aril indolizidínico a partir de α-clorocetonas derivadas da (S)-prolina: síntese da (S)-desoxiipalbidina." Universidade de São Paulo, 2014. http://www.teses.usp.br/teses/disponiveis/75/75133/tde-03072014-144521/.
Full textThe basic structure of indolizidine alkaloids is formed by a five and sixmembered bicyclic ring containing one nitrogen atom shared at the 4 position. This ring system has great prominence among the alkaloids, it is present in a large number of compounds and possess interesting biological profiles. Ipalbidine, for example, is an indolizidine alkaloid with analgesic and anti-oxidant properties. Although this compound has a relatively simple chemical structure, only four enantioselective synthesis are described for this compound. Thus, this dissertation aims to study a new synthetic strategy that allows the preparation of (+)-ipalbidine, as well as other alkaloids having the system 4- azabicyclo[4.3.0]non-3-ene with a phenolic substituent in position 3. A possible interesting route for the synthesis of these alkaloids is to obtain the indolizidine skeleton from a cyclization reaction using a functionalized α-chloroketone (derivative of protected (S)-prolinal (Boc and Cbz)). The key steps of this strategy are: an olefination reaction (Wittig), the preparation of α-chloroketones, addition of aryl group to the α-chloroketones and converting them into the indolizidine skeleton by a cyclization reaction. The α-chloroketones were prepared with overall yields varying from 56 % (Cbz) to 81% (Boc) starting from protected (S)-prolinal in just three steps: olefination reaction , followed by a reduction reaction of the obtained olefin and preparation of the α-chloroketone from an ester . The addition step of the aryl group to α-chloroketone was obtained for both Boc (40%) and Cbz (42%) groups. The Boc-protected α-chloroalcohol was converted to indolizidine skeleton through an \"one-pot\" deprotection reaction, followed by a cyclization reaction (80 %). The cyclization product, in turn, was converted to the novel (+)-ipalbidine analog, (S)-desoxyipalbidine (30 %). This strategy led to the synthesis of (S)-desoxyipalbidine in 6 steps and overall yield of 8 %. It is noteworthy that this type of approach using α-chloroketones was never employed in the synthesis of indolizidine alkaloids, and that strategy can be applied also to the total synthesis of (+)-ipalbidine and other indolizidine alkaloids such as phenanthroindolizidine.
Davis, Jonathan C. "Section one : photochemical methodologies towards the pyrrolizidine and indolizidine alkaloid skeleta; section two; synthesis of novel leukotriene photoaffinity labels." Thesis, University of Reading, 1997. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.360717.
Full textOutin, Johanne. "Synthèse de composés polycycliques azotés par cyclisation de Vilsmeier-Haack et cyclisation de Mannich organocatalysée en séquence." Thèse, Université de Sherbrooke, 2017. http://hdl.handle.net/11143/10979.
Full textCHALARD, PIERRE. "Cyclisation d'allylsilanes chiraux sur des ions n-acyliminium. Syntheses totales enantioselectives des ()-lasubines i et ii, (+)-subcosine ii et ()-indolizidine 167b." Clermont-Ferrand 2, 1999. http://www.theses.fr/1999CLF22093.
Full textTeodoro, Bruno Vinicius Motta 1985. "Síntese de núcleos indolizidínicos a partir de adutos de Morita-Baylis-Hillman. Avaliação de uma metodologia para a dessimetrização de adutos de Morita-Baylis-Hillman." [s.n.], 2014. http://repositorio.unicamp.br/jspui/handle/REPOSIP/250238.
Full textDissertação (mestrado) - Universidade Estadual de Campinas, Instituto de Química
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Resumo: Esta dissertação de mestrado está dividida em duas partes. Na primeira parte descrevemos os resultados obtidos na síntese de núcleos indolizidínicos, a partir de adutos de Morita-Baylis-Hillman (MBH). Na segunda parte, descrevemos os resultados obtidos na avaliação de uma reação de dessimetrização de adutos de MBH. Os núcleos indolizidínicos representam um padrão estrutural de grande interesse sintético, pois existem inúmeros alcaloides, com atividade biológica pronunciada, que contêm este núcleo. A metodologia desenvolvida nesse trabalho permite a preparação de núcleos indolizidínicos, a partir de adutos de MBH, em duas etapas. Assim, uma reação de ciclização intramolecular de um aduto, gera indolizinas que, após uma reação de hidrogenação total, conduz as indolizidinas. A rota desenvolvida é rápida, simples, eficiente e estereosseletiva. Os rendimentos globais variaram de 43 a 55%. Os excessos diastereoisoméricos obtidos variaram entre 68 e 86%, em favor do isômero cis. Nesta parte do trabalho avaliamos também um procedimento para preparar tetraidroindolizinas, a partir da hidrogenação parcial das indolizinas. Usando a mesma estratégia, descrevemos a preparação de tetraidroindolizinas com rendimentos que variaram entre 40-93%. Na segunda parte desse trabalho avaliamos uma alternativa de dessimetrização de adutos de MBH. A redução de ?-ceto-?-metileno-ésteres, obtidos a partir de uma reação de oxidação de adutos de MBH racêmicos, nos permite acessar a esses adutos em suas formas enantiomericamente puras. Após realizar uma triagem de catalisadores de redução assimétrica, a melhor condição encontrada nos forneceu o aduto de MBH enantioenrriquecidos, com um rendimento de 25% e um excesso enantiomérico de 68%, utilizando o catalisador CBS. A partir deste dado, outros estudos poderão ser realizados visando verificar a generalidade do método desenvolvido
Abstract: This work is divided in two parts. In the first part, we described the development of a strategy for preparing indolizidine skeletons starting from Morita-Baylis-Hillman (MBH) adducts. In the second part, the preliminary results of study for the desymmetrization of MBH adducts is reported. The indolizidine core is a structural pattern of great synthetic interest since it's present in the structure of several alkaloids with remarkable biological activity. The two-step methodology developed in this work allowed the efficient preparation of indolizidine nucleus from MBH adducts. Thus, an intramolecular cyclization reaction of MBH adducts derived from 2-pyridine-carboxaldehyde followed by platinum mediated hydrogenation affords the indolizidines in good overall yield. The developed methodology is simple, fast and stereoselective. The overall yields ranged from 43 and 55% and the diastereoisomeric excesses obtained ranged from 68 to 86%, in favor of the cis isomer. The partial hydrogenation of the indolizines allowed the preparation of tetrahydroindolizines. Thus, using the same strategy, we also described the preparation of tetrahydroindolizines with yields ranging from 40-93 %. In the second part of this work we described the preliminary results of an evaluation of an alternative desymmetrization strategy of MBH adducts. The reduction of ?-keto-?-methylene esters obtained from an oxidation of racemic MBH adducts could allow us to access these adducts in their enantiomerically pure forms. A screening of asymmetric reduction catalysts showed us that the CBS catalyst provided the best condition. An enantioenriched MBH adduct was obtained in 25% yield and 68% enantiomeric excess. This result will stimulate new studies in order to check the scope of this method
Mestrado
Quimica Organica
Mestre em Química
Pinho, Vagner Dantas. "Abordagens divergentes na preparação de alcaloides indolizidínicos." Universidade de São Paulo, 2013. http://www.teses.usp.br/teses/disponiveis/75/75133/tde-30072013-093827/.
Full textHerein were described three diverted oriented approaches for the construction of the bicyclic scaffold of indolizidines alkaloids, that figures between one of the most important classes of natural products. In the first approach, a new method to prepare α,β - unsaturated diazoketones was described using the Horner-Wadsworth-Emmons (HWE) reaction between diazophosphonate and aldehydes. The unsaturated diazoketones were used as powerful plataforms to construct the indolizidine carbocyclic scaffold, enploying the Wolff rearrangement as the key step. The second approach was the development of a reductive coupling between α-aminocarbonyl derivatives and methyl acrylate, mediate by SmI2, from this approach, the well-known advanced intermediate for the synthesis of (-)-pumiliotoxin 251D e of the (+/-)-epiquinamide was obtained in only two steps. The third approach uses the intermolecular Wittig/HWE reaction as the key step in the construction of a bicyclic intermediate containing an α,β -unsaturated moiety that could be used for a diverted oriented approach in the indolizidine alkaloids synthesis.
Conegero, Leila de Souza. "Estudos visando a sintese de alcaloides pirrolizidinicos e indolizidinicos : aproveitamento da (+)-retronecina e do acido D-isoascorbico." [s.n.], 2006. http://repositorio.unicamp.br/jspui/handle/REPOSIP/249280.
Full textTese (doutorado) - Universidade Estadual de Campinas, Instituto de Quimica
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Resumo: O trabalho desenvolvido visou a obtenção de alcalóides pirrolizidínicos e indolizidínicos utilizando a (+)-retronecina (1) e o ácido D-isoascórbico (35D) como matérias primas, respectivamente. A retronecina (1) foi isolada da espécie vegetal Senecio brasiliensis. Para a preparação da base necínica (1R,6S,7S,8R)-7- (hidroximetil)-hexaidro-1H-pirrolizina-1,6-diol (37), a retronecina (1) foi submetida à reação de epoxidação com ácido meta-cloroperbenzóico. A a-epóxi-retronecina (44), após proteção das hidroxilas com cloreto de tercbutildimetilsilila, foi submetida à abertura com níquel de Raney, e a posterior desproteção forneceu o triol 37, que foi obtido em 5 etapas e 15 % de rendimento. Os compostos (1R,2R,7R,8S)-1-(hidroximetil)-hexaidro-1H-pirrolizina-1,2,7-triol (39) e a platinecina (72) foram preparados a partir de reações de diidroxilação e hidrogenação estereosseletiva da retronecina (1) em 70 e 86 % de rendimento, respectivamente. A abordagem síntética inicial para obtenção de alcalóides indolizidínicos foi baseada na adição do 2-terc-butildimetilsililoxifurano (94) ao íon N-acilimínio derivado da lactama 90. Em função do moderado rendimento e da modesta diastereosseletividade obtida foi proposta uma segunda abordagem sintética para obtenção de indolizidinas. Os alcalóides indolizidínicos, (1R,2S,8aR)- octaidroindolizina-1,2-diol (100) (ent-epi-lentiginosina) e (1R,2S,6R,7S,8aR)- octaidroindolizina-1,2,6,7-tetrol (101) foram preparados a partir da lactona 77. Os compostos 100 e 101 foram obtidos do intermediário-chave 82, que foi preparado a partir da adição de alilamina à lactona 77, derivada do ácido isoascórbico. Em seguida a hidroxiamida 82 foi oxidada à hidroxilactama correspondente, que foi submetida à reação de acetilação fornecendo o composto 91. Reação de alilação de 91, seguido de metátese de olefinas forneceu a indolizidinona 99. Reação de hidrogenação/hidroxilação de 99, redução da lactama e desproteção do acetal levou ao diol 100 e ao tetrol 101 em rendimentos de 27 e 31 %, respectivamente, a partir da lactona 77
Abstract: The aim of the present work was the synthesis of pyrrolizidine and indolizidine alkaloids using (+)-retronecine (1) and D-isoascorbic acid (35D) as starting materials, respectively. Retronecine (1) was isolated from the vegetal species Senecio brasiliensis. The synthesis of the necine base (1R,6S,7S,7aR)-7-(hydroxymethyl)-hexahydro-1H-pirrolizine-1,6-diol (37) was accomplished by the m-chloroperbenzoic acid epoxidation of retronecine (1). After hydroxyl protection with tert-butyldimethylsilyl chloride, epoxide 44 was subjected to ring opening with nickel Raney and deprotection to yield triol 37, in 5 steps and 15 % yield. Compounds (1R,7S,8R)-7-(hydroxymethyl)-hexahydro-1H-pirrolizin-1-ol (39) and platynecine (72) were prepared after stereoselective dihydroxylation and hydrogenation reactions of retronecine (1) in 70 and 86 % yield, respectively. The first approach to the synthesis of indolizidine alkaloids was based on the 2-tert-butyldimethylsilyloxyfuran addition to lactam 90-derived N-acyliminium ion. Due to moderate yield and diastereoselectivity obtained, a second synthetic approach to the synthesis of indolizidines was suggested. Indolizidine alkaloids 100 and 101 were prepared from lactone 77. Compounds 100 and 101 were obtained from key intermediate 82, which was prepared from allylamine addition to isoascorbic acid-derived lactone 77. Following that, hydroxyamide 82 was oxidized to the corresponding hydroxylactam which was subjected to acetylation, yielding compound 91. Allylation of 91 and subsequent ring closing olefin metathesisyielded indolizidinone 99. Hydrogenation/hydroxylation reaction of 99 followed by lactam reduction and deprotection of acetonide provided diol 100 and tetrol 101, in 27 and 31 % yield, respectively, from lactone 77
Doutorado
Quimica Organica
Doutor em Ciências
Dener, Jeffrey Mark. "Part I, the enantioselective synthesis of pyrrolizidine alkaloids using alpha-acylamino radical cyclizations ; Part II, the enantioselective synthesis of the indolizidine alkaloid (-)-swainsonine using an alpha-acylamino radical cyclization /." The Ohio State University, 1988. http://rave.ohiolink.edu/etdc/view?acc_num=osu1487591658176567.
Full textPereira, Elaine. "Adição de enolatos de titanio derivados de N-acil-(4S)-4-isopropil-1,3-tiazolidin-2-tiona a ions N-aciliminios ciclicos : sintese assimetrica dos alcaloides (+)-isoretronecanol e (+)-5-epi-tashiromina." [s.n.], 2005. http://repositorio.unicamp.br/jspui/handle/REPOSIP/249250.
Full textDissertação (mestrado) - Universidade Estadual de Campinas, Instituto de Quimica
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Mestrado
Quimica Organica
Mestre em Química
Buckley, L. "Transition Metal Approaches to Indolizidines." Thesis, Queen's University Belfast, 2010. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.527666.
Full textThompson, Stephen Harold James. "Synthetic approaches towards polyhydroxylated indolizidines." Thesis, University of Bristol, 1994. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.260223.
Full textHoward, Steven. "The synthesis of polyhydroxy indolizidines." Thesis, University of Cambridge, 1994. https://www.repository.cam.ac.uk/handle/1810/272794.
Full textGiles, Melvyn Edward. "Novel synthetic approaches to polyhydroxylated indolizidines." Thesis, University of Bath, 1991. https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.760620.
Full textBeck, Daniel Antony Speedie, and beckautomatic@gmail com. "Stereoselective intramolecular Michael addition reactions of pyrrole and their application to natural product syntheses." The Australian National University. Research School of Chemistry, 2006. http://thesis.anu.edu.au./public/adt-ANU20070130.130009.
Full textCollins, Ian James. "Studies towards the synthesis of polyhydroxylated indolizidines." Thesis, University of Cambridge, 1991. https://www.repository.cam.ac.uk/handle/1810/272578.
Full textCélimène, Catherine. "Voie d'acces generale aux indolizidines 3,5-disubstituees via des acyliminiums derives de la l-proline : syntheses generales des indolizidines (-) 195b, (-) 223ab et (-) 239ab." Paris 6, 1995. http://www.theses.fr/1995PA066556.
Full textSibley, A. William. "Slaframine, australines and castanospermines." Thesis, University of Nottingham, 1997. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.363593.
Full textMeldrum, Kevin Patrick. "Functionalized cyclic nitrones in the synthesis of polyhydroxylated pyrrolizidines and indolizidines." Thesis, Heriot-Watt University, 1997. http://hdl.handle.net/10399/660.
Full textFletcher, Rodney Justin. "Radical cyclisation in routes to cis-fused heterocycles." Thesis, University of Nottingham, 1995. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.283701.
Full textLombart, Henry-Georges. "Développement d'un nouvel aminé indolizidinone et applications en mimétique peptidique." Thesis, National Library of Canada = Bibliothèque nationale du Canada, 1998. http://www.collectionscanada.ca/obj/s4/f2/dsk2/ftp03/NQ33047.pdf.
Full textIkhiri, Halid. "Alcaloïdes pyrrolizidiniques de Hugonia oreogena et H. Penicillanthemum (Linacées) : détermination structurale et synthèse : étude ethnobotanique des plantes de la pharmacopée traditionnelle au Niger et détermination structurale de constituants de l'une d'elles, Ipomoea muricata (Convolvulacées)." Paris 11, 1987. http://www.theses.fr/1987PA112172.
Full textRasmussen, Martin Ohsten. "Nouvelle approche asymetrique des indolizidines polyhydroxylees : synthese de la (+)-lentiginosine et de la (-)-2-epilentiginosine." Université Joseph Fourier (Grenoble), 2001. http://www.theses.fr/2001GRE10059.
Full textRazavi, Hossein. "Amino acid Schiff base methodology for the synthesis of glycosidase inhibitors: Polyhydroxylated pyrrolidines and indolizidines." Diss., The University of Arizona, 1999. http://hdl.handle.net/10150/284049.
Full textBohland, Frank [Verfasser]. "Stereoselektive Synthese von polyhydroxylierten Indolizidinderivaten – Aufbau optisch aktiver Indolizidinon-carbamide / Frank Bohland." Mainz : Universitätsbibliothek Mainz, 2017. http://d-nb.info/1133223214/34.
Full textMaloney, Kevin M. (Kevin Matthew). "[4+2] cycloadditions of iminoacetonitriles : a general strategy for the synthesis of quinolizidines, indolizidines, and piperidines." Thesis, Massachusetts Institute of Technology, 2007. http://hdl.handle.net/1721.1/39739.
Full textVita.
Includes bibliographical references.
Iminoacetonitriles participate as reactive dienophiles in intermolecular and intramolecular Diels-Alder cycloadditions leading to quinolizidines, indolizidines, and piperidines. The resultant a-amino nitrile cycloadducts are versatile synthetic intermediates which can be further elaborated by stereoselective alkylation, reduction, reductive cyclization, and Bruylants reactions. The first part of this thesis describes the full details of our studies on the synthesis of iminoacetonitriles, the scope of their Diels-Alder reactions, and the synthetic elaboration of the a-amino nitrile cycloadducts to provide access to a variety of substituted quinolizidine and indolizidine derivatives. The second part of this thesis reports on the total synthesis of quinolizidine (-)-217A and our efforts directed toward the total synthesis of indolizidine (-)-235B'.
by Kevin M. Maloney.
Ph.D.
Souza, Barbara Bernardim de. "Síntese de indolizidinas e quinolizidinas diidroxiladas a partir de diazocetonas α,β-insaturadas." Universidade de São Paulo, 2013. http://www.teses.usp.br/teses/disponiveis/75/75133/tde-23042013-112347/.
Full textPolyhydroxylated Indolizidine, quinolizidine and piperidine alkaloids represent classes of compounds widely investigated in the chemical community. This fact is due to their pronounced biological activities as glycosidase inhibitors. Considering that, many research groups have been developing new synthetic methodologies to obtain these alkaloids and analogs effectively and in few steps. This work presents a synthetic route for the preparation of dihydroxylated indolizidine and quinolizidine alkaloids from α,β-unsaturated diazoketones. The strategy for the synthesis of these compounds is based on the same methodology to construct the indolizidine and quinolizidine skeleton. The key steps involve a Horner-Wadsworth-Emmons (HWE) olefination reaction from aminoaldehydes, followed by a Wolff Rearrangement. As the starting material to construct the indolizidine skeleton, Cbz-S-prolinal was employed. This aminoaldehyde is also the source of the stereogenic center and one of the rings present in the final structure. The coupling reaction (HWE reaction) between Cbz-S-prolinal and a diazophosphonate (methodology recently described by our research group) has provided an α,β-unsaturated diazoketone in 67% yield. This compound was then subjected to a Wolff Rearrangement, providing a β,γ-unsaturated ester in 96% yield. This advanced intermediate was functionalized through a high selective dihydroxylation reaction, furnishing a hydroxylated lactone in 66% yield. The synthesis was then completed employing an intramolecular cyclization reaction (94% yield), followed by lactam reduction to provide the dihydroxylated indolizidine (1,6-dideoxyepicastanospermine) in 71% yield. For the construction of the quinolizidine skeleton, was employed racemic Cbz-pipecolinal as the starting material. From the olefination reaction, the corresponding α,β-unsaturated diazoketone was obtained in 91% yield. After a Wolff Rearrangement (95%), dihydroxylation reaction (75%), cyclization (54-74%) and lactam reduction (87-90%), two novel dihydroxylated quinolizidines could be synthesized. These indolizidine and quinolizidine alkaloids may be evaluated as new inhibitors of glycosidases.
Vidal, Virginie. "Synthèse asymétrique d'analogues d'alcaloïdes pipéridiniques et indolizidiniques à l'aide d'un synthon chiral dérivé d'amino-acide." Paris 11, 1988. http://www.theses.fr/1988PA112316.
Full textThe 2S cyano 6S oxazolo piperidine (synthon) which is obtained in one step starting from R(-) phenylglycinol, glutaraldehyde and potassium cyanide allows regio and stereoselective alkylations at the C-2 position of the piperidine ring. This thesis describes the usage of this compound in the asymmetric synthesis of severa] products from the piperidinic and indolizidini c series. Alkylation of the synthon I with dibromopropane permitted to obtain, after cyclisation of nitrogen on brome and elimination of the auxiliar chiral chain the first asymmetric synthesis of (-)-delta coniceine in three steps. Reaction of synthon 1 with ethyl chloroformate followed by a reduction with sodium borohydride and hydrogenolysis leads to R(-) pipecolinol. The reaction of the anion of the synthon on aldehydes was studied, in particular, it leads with a high stereoselectivity to beta amino alcohols. The preparation of (+)-beta -conhydrine was thus carried out by alkylation of 1 with propionaldehyde and permitted in this way the determination of the absolute configuration of this product. Following this strategy, an asymmetric synthesis of an indolizidine diol, a natural product analog (swainsonine), inhibitor of alpha mannosidase , was achieved. Alkylation of synthon 1 with crotonaldehyde followed by decyanation with sodium borohydride and epoxydation supplies after cyclisation of the nitrogen atom on the epoxide a swainsonine analog
González, Soria María José. "Selective synthesis and reactivity of indolizines." Doctoral thesis, Universidad de Alicante, 2018. http://hdl.handle.net/10045/98672.
Full textMiaskiewicz, Solène. "Or et azacycles : vers la synthèse totale de molécules naturelles." Thesis, Strasbourg, 2017. http://www.theses.fr/2017STRAF006/document.
Full textNature is a nearly endless source of molecules, often possessing remarkable biological properties. Thus, plants provide new structures every day, inspiring chemists to synthetically create similar molecules or analogs, which are potential therapeutic agents for example. The emergence of organometallic chemistry allowed for considerable improvement of synthetic methods to make complex molecular scaffolds. Homogeneous gold catalysis, whose potential has only been explored starting from 2000, proved its efficiency to make numerous reactions. Most of them can generate several carbon-carbon or carbon-heteroatom bonds in one step. Soft conditions as well as good tolerance of gold catalysts toward multiple functional groups naturally led to the application of gold-catalyzed steps in various total syntheses of natural products.The present study evolves in this context and explores the reactivity of strained azacycles and alkynes in the presence of gold(I) to form heterocyclic skeletons that are commonly found in natural products. The specific reactivity of sulfonyl nitrogen-protecting groups has also been studied to synthesize azabicyclic compounds. The application of those various new methodologies to the synthesis of target molecules has finally been studied
Faria, Antonio Rodolfo de. "Sintese de indolizidinas e pirrolizidinas via reação de cicloadição [2+2] de enecarbonatos endociclicos com alquilcetenos e halo-alquilcetenos." [s.n.], 1996. http://repositorio.unicamp.br/jspui/handle/REPOSIP/249870.
Full textTese (doutorado) - Universidade Estadual de Campinas, Instituto de Quimica
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