Relevant bibliographies by topics / Spiroketals

Academic literature on the topic 'Spiroketals'

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Published: 4 June 2021
Last updated: 10 February 2022

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Journal articles on the topic "Spiroketals"

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Čikoš, Ana, Irena Ćaleta, Dinko Žiher, Mark B. Vine, Ivaylo J. Elenkov, Marko Dukši, Dubravka Gembarovski, et al. "Structure and conformational analysis of spiroketals from 6-O-methyl-9(E)-hydroxyiminoerythronolide A." Beilstein Journal of Organic Chemistry 11 (August 19, 2015): 1447–57. http://dx.doi.org/10.3762/bjoc.11.157.

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Three novel spiroketals were prepared by a one-pot transformation of 6-O-methyl-9(E)-hydroxyiminoerythronolide A. We present the formation of a [4.5]spiroketal moiety within the macrolide lactone ring, but also the unexpected formation of a 10-C=11-C double bond and spontaneous change of stereochemistry at position 8-C. As a result, a thermodynamically stable structure was obtained. The structures of two new diastereomeric, unsaturated spiroketals, their configurations and conformations, were determined by means of NMR spectroscopy and molecular modelling. The reaction kinetics and mechanistic aspects of this transformation are discussed. These rearrangements provide a facile synthesis of novel macrolide scaffolds.
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Messerle, Barbara A., and Khuong Q. Vuong. "Synthesis of spiroketals by iridium-catalyzed double hydroalkoxylation." Pure and Applied Chemistry 78, no. 2 (January 1, 2006): 385–90. http://dx.doi.org/10.1351/pac200678020385.

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A highly efficient approach to the synthesis of spiroketals involves the double cyclization of alkynyl diols using transition-metal catalysts. The iridium complex [Ir(PyP)(CO)2]BPh4 where PyP = 1-[(2-diphenylphosphino)ethyl]pyrazole is an effective catalyst for promoting the formation of spiroketals via this double hydroalkoxylation reaction. The complex promotes the formation of a series of spiroketal products from alkynyl diol starting materials such as 3-ethynylpentane-1,5-diol and 2-(4-hydroxybut-1-ynyl)benzyl alcohol. Stereoselective cyclization occurs for 3-ethynylpentane-1,5-diol, 3-ethynylhexane-1,6-diol. The cycloadditions occur in all but one case with quantitative conversion in under 24 h at 120 °C.
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Brimble, Margaret A., and Seng H. Chan. "Synthesis of 7-Methoxy-3′,4′,5′,6′-tetrahydrospiro-[isobenzofuran-1(3H),2′-pyran]-3-one and 5,7-Dimethoxy-3′,4′,5′,6′-tetrahydrospiro[isobenzofuran-1(3H),2′-pyran]-3-one." Australian Journal of Chemistry 51, no. 3 (1998): 235. http://dx.doi.org/10.1071/c97193.

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The synthesis of novel aryl spiroketals, which contain a similar substitution pattern to that present in the antifungal agents the papulacandins, is described. Thus, spiroketal (7) was obtained from acid-catalysed cyclization of the keto alcohol (13), and spiroketal (8) was obtained from acid-catalysed cyclization of keto alcohols (12) and (19). Keto alcohols (12), (13) and (19) in turn were prepared by ortho-directed lithiation of amides (10), (11) and oxazoline (17) respectively, followed by reaction with δ-valerolactone. Substitution of the aromatic ring occurred at the sterically hindered position ortho to both the methoxy and ortho-directing metalation group. In an alternative approach to the synthesis of the desired spiroketals, two palladium(0)-catalysed coupling strategies were examined. The Stille coupling between the aryl stannane (24) and iodoglucal (25) resulted in a low yield of the aryl C-glycoside (21). Likewise, a low yield for the same coupled product (21) was achieved by a Suzuki coupling between the arylboronic acid (26) and iodoglucal (25).
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Tlais, Sami F., and Gregory B. Dudley. "On the proposed structures and stereocontrolled synthesis of the cephalosporolides." Beilstein Journal of Organic Chemistry 8 (August 14, 2012): 1287–92. http://dx.doi.org/10.3762/bjoc.8.146.

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The synthesis of four candidate stereoisomers of cephalosporolide H is described, made possible by a zinc-chelation strategy for controlling the stereochemistry of oxygenated 5,5-spiroketals. The same strategy likewise enables the first stereocontrolled synthesis of cephalosporolide E, which is typically isolated and prepared admixed with its spiroketal epimer, cephalosporolide F.
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Green, Jason C., G. Leslie Burnett, and Thomas R. R. Pettus. "New strategies for natural products containing chroman spiroketals." Pure and Applied Chemistry 84, no. 7 (May 2, 2012): 1621–31. http://dx.doi.org/10.1351/pac-con-11-10-34.

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Two cycloaddition strategies are described that lead to various chroman spiroketals from assorted exocyclic enol ethers. Unlike conventional thermodynamic ketalization strategies, the stereochemical outcome for this approach is determined by a kinetic cycloaddition reaction. Thus, the stereochemical outcome reflects the olefin geometry of the starting materials along with the orientation of the associated transition state. However, the initial kinetic product can also be equilibrated by acid catalysis and reconstituted into a thermodynamic stereochemical arrangement. Thus, these strategies uniquely enable synthetic access to either the thermodynamic or kinetic conformation of the spiroketal stereocenter itself. Applications of these strategies in the syntheses of berkelic acid, β-rubromycin, and paecilospirone are presented along with the use of a chroman spiroketal for the construction of heliespirones A and C.
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Lee, Seongmin, and Philip L. Fuchs. "In situ nitrosonium ion generation — α-Oximinylation of enol ethers from steroidal spiroketals: Introduction of C23 (R)-OH in cephalostatin intermediates." Canadian Journal of Chemistry 84, no. 10 (October 1, 2006): 1442–47. http://dx.doi.org/10.1139/v06-113.

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Nitrosonium ion generated in situ from the reaction of t-BuNO2 and BF3·Et2 is an effective oximinylating agent for enol ethers derived from steroidal spiroketals. The scope and limitations of this method has been studied. The difficult reduction of C23 ketone to C23 (R)-alcohol has now been selectively achieved via L-Selectride® reduction. Application to cephalostatin intermediates is discussed.Key words: oximinylation, nitrosonium ion, steroid spiroketal, cephalostatins.
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Tlais, Sami F., and Gregory B. Dudley. "A gold-catalyzed alkyne-diol cycloisomerization for the synthesis of oxygenated 5,5-spiroketals." Beilstein Journal of Organic Chemistry 7 (May 4, 2011): 570–77. http://dx.doi.org/10.3762/bjoc.7.66.

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A highly efficient synthesis of oxygenated 5,5-spiroketals was performed towards the synthesis of the cephalosporolides. Gold(I) chloride in methanol induced the cycloisomerization of a protected alkyne triol with concomitant deprotection to give a strategically hydroxylated 5,5-spiroketal, despite the potential for regiochemical complications and elimination to furan. Other late transition metal Lewis acids were less effective. The use of methanol as solvent helped suppress the formation of the undesired furan by-product. This study provides yet another example of the advantages of gold catalysis in the activation of alkyne π-systems.
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Perron, Francoise, and Kim F. Albizati. "Chemistry of spiroketals." Chemical Reviews 89, no. 7 (November 1989): 1617–61. http://dx.doi.org/10.1021/cr00097a015.

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Balachandran, Raghavan, Tamara D. Hopkins, Catherine A. Thomas, Peter Wipf, and Billy W. Day. "Tubulin-Perturbing Naphthoquinone Spiroketals." Chemical Biology & Drug Design 71, no. 2 (February 2008): 117–24. http://dx.doi.org/10.1111/j.1747-0285.2007.00616.x.

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Ardes-Guisot, Nicolas, Bani Ouled-Lahoucine, Isabelle Canet, and Marie-Eve Sinibaldi. "A straightforward route to spiroketals." Tetrahedron Letters 48, no. 48 (November 2007): 8511–13. http://dx.doi.org/10.1016/j.tetlet.2007.09.151.

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Dissertations / Theses on the topic "Spiroketals"

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Selvaraj, Peter Rajan. "Exploratory study of ionophoric spiroethers and spiroketals." Columbus, Ohio : Ohio State University, 2006. http://rave.ohiolink.edu/etdc/view?acc%5Fnum=osu1158620953.

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Owen, David Rodney. "Zirconocene mediated co-cyclisation reactions." Thesis, University of Southampton, 2000. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.313216.

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Selvaraj, Peter Rajan. "Exploratory study of ionophoric spiroethers and spioketals." The Ohio State University, 2006. http://rave.ohiolink.edu/etdc/view?acc_num=osu1158620953.

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Modolo, Isabelle. "Studies toward completion of the C1-C28 segment of spongistatin 1. Synthesis and photochemistry of 4bH-pyrido[2,1-a]isoindol-6-one." The Ohio State University, 2009. http://rave.ohiolink.edu/etdc/view?acc_num=osu1236277748.

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Salles, Junior Airton Gonçalves 1977. "Síntese total dos ácidos pterídicos A e B." [s.n.], 2009. http://repositorio.unicamp.br/jspui/handle/REPOSIP/248482.

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Orientador: Luiz Carlos Dias
Tese (doutorado) - Universidade Estadual de Campinas, Instituto de Química
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Resumo: Este trabalho relata a síntese total dos ácidos pterídicos A e B. O plano sintético utiliza como etapa-chave a reação aldólica syn com adição anti-Felkin intermediada por enolato de lítio entre a etil cetona a,b-insaturada de geometria Z 5 e o aldeído 4 para obtenção do fragmento C5-C15. Até onde sabemos este é o primeiro exemplo da utilização de um enolato de uma etil cetona a,b-insaturada quiral com geometria Z em uma reação aldólica. Uma eficiente reação de espirocetalização seguida de transformações adicionais conduziu ao ácido pterídico A em 2,9% de rendimento global para 13 etapas e ao ácido pterídico B em 2,8% de rendimento global também para 13 etapas. Em relação às outras sínteses totais, esta rota sintética apresenta um rendimento global comparável, mas chama a atenção pela nova e interessante abordagem na obtenção do fragmento C5-C15 via reação aldólica intermediada por lítio
Abstract: This work describes the convergent stereoselective synthesis of pteridic acids A and B. Our strategy involved a lithium enolate-mediated aldol reaction between ethyl ketone 5 and aldehyde 4 as the key step to set up C5-C15 fragment favoring 1,2-syn anti-Felkin adduct. As far we know, this is the first example of an aldol reaction between a chiral enolate of a (Z) enone and a chiral aldehyde. Efficient spiroketalization followed by additional transformations provided pteridic acids A and B in 2.9% and 2.8% overall yields, respectively. This approach compares very well with previously published routes and attracts attention to the novel and interesting C9-C10 bond construction to obtain C5-C15 fragment
Doutorado
Quimica Organica
Doutor em Ciências
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Oliveira, Luciana Gonzaga de. "Sintese total das (+)-crocacinas C e D : sintese dos fragmentos 6,6-espirocetal das espirofunginas A e B." [s.n.], 2004. http://repositorio.unicamp.br/jspui/handle/REPOSIP/248479.

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Orientador: Luiz Carlos Dias
Tese (doutorado) - Universidade Estadual de Campinas, Instituto de Quimica
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Doutorado
Quimica Organica
Doutor em Quimica
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Borghese, Sophie. "Toward green processes organic synthesis by catalysis with metal-doped solids." Phd thesis, Université de Strasbourg, 2013. http://tel.archives-ouvertes.fr/tel-01017796.

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Nowadays, the modern chemical industry has to deal with increasing environmental concerns, including the disposal of waste and its economic impact, or the diminution of important worldwide resources such as transition metals. In this Ph.D. thesis, we aimed to bring improvement in this area by the development of green processes, based on the use of recyclable heterogeneous catalysts. By combining the catalytic properties of several metal cations with the properties of solid catalysts such as polyoxometalates or zeolites, we were able to set up new tools for organic synthesis. Silver-doped polyoxometalates proved to be very efficient catalysts in the rearrangement of alkynyloxiranes to furans. Acetals and spiroketals were synthetized by dihydroalkoxylation of alkynediols under catalysis with silver-zeolites. As a perspective, we highlighted the potential applications of such green procedures in the total synthesis of more complex molecules. The first results suggested that these environmental friendly processes should gain increasing interest in the future.
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Lipinski, Radoslaw Michal. "Synthesis of the ABC fragment of pectenotoxin-4." Thesis, University of Oxford, 2012. http://ora.ox.ac.uk/objects/uuid:123bf4c1-844a-492a-abdb-f7555719d7ff.

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This thesis details the application of two synthetic methodologies, developed by the Donohoe group, to the synthesis of the ABC fragment of pectenotoxin-4, a macrolide marine natural product that consists of 19 stereogenic centres, three tetrahydrofuran rings, one spiroketal and one bicyclic ketal embedded within a 26-membered macrocycle. Pivotal to the developed synthetic route was the utilisation of an unprecedented cascade osmium catalysed oxidative cyclisation for the construction of two THF rings (the BC ring system). After successfully developing a model system for the synthesis of the AB anomeric 6,5 spiroketal, which involved the employment of a hydride shift initiated oxo carbenium ion formation followed by intramolecular spiroketalisation, the developed system was then applied to the fully elaborated synthesis of the ABC fragment. The synthesis of the ABC fragment of pectenotoxin-4 was completed in 20 linear steps, with an overall yield of 3.3%.
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Vuong, Khuong Quoc Chemistry Faculty of Science UNSW. "Metal complex catalysed C-X (X = S, O and N) bond formation." Awarded by:University of New South Wales. Chemistry, 2006. http://handle.unsw.edu.au/1959.4/23015.

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This thesis describes the catalysed addition of X-H bonds (X = S, O and N) to alkynes using a range of novel rhodium(I) and iridium(I) complexes containing hybrid bidentate phosphine-pyrazolyl, phosphine-imidazolyl and phosphine-N heterocyclic carbene (NHC) donor ligands. The synthesis of novel bidentate phosphine-pyrazolyl, phosphine-imidazolyl (P-N) and phosphine-NHC (PC) donor ligands and their cationic and neutral rhodium(I) and iridium(I) complexes [M(P N)(COD)]BPh4, [M(PC)(COD)]BPh4, [Ir(P-N)(CO)2]BPh4 and [M(P-N)(CO)Cl] were successfully performed. An unusual five coordinate iridium complex with phosphine-NHC ligands [Ir(PC)(COD)(CO)]BPh4 was also obtained. Seventeen single crystal X-ray structures of these new complexes were determined. A range of these novel rhodium and iridium complexes were effective as catalysts for the addition of thiophenol to a variety of alkynes. Iridium complexes were more effective than rhodium analogues. Cationic complexes were more effective than neutral complexes. Complexes with hybrid phosphine-nitrogen donor were more effective than complexes containing bidentate nitrogen donor ligands. An atom-economical, efficient method for the synthesis of cyclic acetals and bicyclic O,O-acetals was successfully developed based on the catalysed hydroalkoxylation. Readily prepared terminal and non-terminal alkyne diols were cyclised into bicyclic O,O-acetals in quantitative conversions in most cases. The efficiency of a range of rhodium and iridium complexes containing bidentate P-N and PC donor ligands as catalysts for the cyclisation of 4-pentyn-1-amine to 2-methyl-1-pyrroline varied significantly. The cationic iridium complexes with the bidentate phosphine-pyrazolyl ligands, [Ir(R2PyP)(COD)]BPh4 (2.39-2.42) were extremely efficient as catalysts for this transformation. Increasing the size of the substituent on or adjacent to the donor led to improvement in catalytic activity of the corresponding metal complexes. The mechanism of the catalysed hydroalkoxylation was proposed to proceed by the initial activation of the alkyne via ?? coordination to the metal centre. The ?? binding of both aliphatic and aromatic alkynes to [Ir(PyP)(CO)2]BPh4 (2.44) was observed by low temperature NMR and no reaction between 2.44 and alcohols was observed. In contrast, the facility in which thiol and amine oxidatively added to 2.44 led the proposal that in the hydrothiolation and hydroamination reaction, the catalytic cycle commences with the activation of the X-H bond (X = S, N) by an oxidative addition process.
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Baddeley, Kate. "Ortholactone spiroketal fragment coupling." Thesis, Queen's University Belfast, 2017. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.725334.

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A divergent synthesis of spiroketals has been developed via the coupling of ortholactone and allylsilane fragments. This work expands upon earlier efforts into an intramolecular silyl modified sakurai reaction reported by Marko et al. The route provides a simple approach towards the divergent synthesis of complex structures which could be used in the synthesis of natural products and pharmaceutical molecules. The scope of this reaction has been amplified by the development of a novel methodology towards the synthesis of ortholactones via an oxidative catalytic nucleopalladation system which has allowed for the synthesis of a vast range of synthetically useful and highly functionalised ortholactones from readily accessible dihydropyran building blocks. The utility of these highly functionalised ortholactones is also demonstrated in a stereoselective rearrangement to form a substantial number of gamma-lactone structures, which are a common motif in a wide variety of natural products.
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Books on the topic "Spiroketals"

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Warrier, Ulhas S. Synthesis of a model of the spiroketal portion of avermectin B. 1987.

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Book chapters on the topic "Spiroketals"

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Sridhar, Perali Ramu. "Carbohydrate-Derived Spiroketals and Spirocyclic Lactones." In Topics in Heterocyclic Chemistry, 105–36. Cham: Springer International Publishing, 2019. http://dx.doi.org/10.1007/7081_2019_32.

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Vaillancourt, Valerie, Norman E. Pratt, Françoise Perron, and Kim F. Albizati. "The Total Synthesis of Spiroketal-Containing Natural Products." In Total Synthesis of Natural Products, 533–691. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2007. http://dx.doi.org/10.1002/9780470129715.ch4.

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Yamamoto, Yoshihiko. "Spiroketal Phthalane C-Glycosides: Synthesis of Papulacandins and SGLT2 Inhibitors." In Topics in Heterocyclic Chemistry, 215–60. Cham: Springer International Publishing, 2019. http://dx.doi.org/10.1007/7081_2018_27.

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Carter, R. G., and D. L. Kuiper. "Spiroketals." In Stereoselective Reactions of Carbonyl and Imino Groups, 1. Georg Thieme Verlag KG, 2011. http://dx.doi.org/10.1055/sos-sd-202-00477.

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Carter, R. G., and D. L. Kuiper. "5,5-Spiroketals." In Stereoselective Reactions of Carbonyl and Imino Groups, 1. Georg Thieme Verlag KG, 2011. http://dx.doi.org/10.1055/sos-sd-202-00478.

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Carter, R. G., and D. L. Kuiper. "5,6-Spiroketals." In Stereoselective Reactions of Carbonyl and Imino Groups, 1. Georg Thieme Verlag KG, 2011. http://dx.doi.org/10.1055/sos-sd-202-00480.

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Carter, R. G., and D. L. Kuiper. "6,6-Spiroketals." In Stereoselective Reactions of Carbonyl and Imino Groups, 1. Georg Thieme Verlag KG, 2011. http://dx.doi.org/10.1055/sos-sd-202-00491.

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Tius, M. A. "Of Spiroketals." In Cumulenes and Allenes, 1. Georg Thieme Verlag KG, 2008. http://dx.doi.org/10.1055/sos-sd-044-00303.

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"Spiroketals (Update 2010)." In Knowledge Updates 2010/3, edited by Ishihara, Procter, Schaumann, Fuerstner, Molander, Schaumann, Anderson, et al. Stuttgart: Georg Thieme Verlag, 2011. http://dx.doi.org/10.1055/sos-sd-129-00062.

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"Product Class 9: Spiroketals." In Category 4, Compounds with Two Carbon Heteroatom Bonds, edited by Warriner. Stuttgart: Georg Thieme Verlag, 2007. http://dx.doi.org/10.1055/sos-sd-029-00536.

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Conference papers on the topic "Spiroketals"

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Bagnoli, Luana, Marcello Tiecco, Lorenzo Testaferri, Catalina Scarponi, Andrea Temperini, Francesca Marini, and Claudio Santi. "Selenium Promoted Enantioselective Synthesis of Spiroketals." In The 9th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2005. http://dx.doi.org/10.3390/ecsoc-9-01519.

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Dos Santos, Alcindo, Jefferson Princival, João Comasseto, and Simone de Barros. "Tellurium / Lithium Exchange Reaction in the Synthesis of Spiroketals and 1,6-dioxigenated Systems." In The 10th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2006. http://dx.doi.org/10.3390/ecsoc-10-01433.

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Spanu, Pietro, Maria Pia Fuggetta, Franco Morelli, Fausta Ulgheri, Francesco Deligia, Giovanni Loriga, Paola Carta, et al. "A new synthetic spiroketal: studies on antitumor activity on murine melanoma model In vivo and mechanism of action In vitro." In 4th International Electronic Conference on Medicinal Chemistry. Basel, Switzerland: MDPI, 2018. http://dx.doi.org/10.3390/ecmc-4-05621.

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