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Dissertations / Theses on the topic 'Squalestatin'

Author: Grafiati
Published: 4 June 2021
Last updated: 13 February 2022

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1

Hassan, Awatef Mahdi. "Synthetic and biosynthetic studies on squalestatin." Thesis, University of Bristol, 1997. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.388330.

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2

Sintim, Herman Ofosuhene. "Synthetic studies towards 6,7-dideoxysqualestatin H5." Thesis, University of Oxford, 2002. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.270739.

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3

Hurley, Déirdre. "Investigations into the squalestatin biosynthetic gene cluster." Thesis, University of Bristol, 2006. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.435424.

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4

Bailey, James Matthew. "Synthetic studies towards zaragozic acid A - squalestatin S1." Thesis, University of Oxford, 1997. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.389086.

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5

Westaway, Susan Marie. "Squalestatin biosynthesis : synthesis and incorporation of assembly intermediates." Thesis, University of Bristol, 1995. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.296602.

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6

Mansfield, Darren James. "Synthetic approaches towards Squalestatin 1 : a potent anti-hypercholesterolemic agent." Thesis, University of Exeter, 1993. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.393292.

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7

Yao, Hao [Verfasser]. "In Vitro investigation of multi-domain fragments of squalestatin tetraketide synthase / Hao Yao." Hannover : Gottfried Wilhelm Leibniz Universität Hannover, 2019. http://d-nb.info/1176105167/34.

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8

Glod, Frank. "PCR generated gene probes for cloning fungal polykeptide synthase genes associated with squalestatin biosynthesis." Thesis, University of Bristol, 2003. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.268525.

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9

Lebe, Karen Elisabeth [Verfasser]. "Investigating the biosynthesis of the fungal metabolites Squalestatin S1, Strobilurin A and SCH–642305 / Karen Elisabeth Lebe." Hannover : Gottfried Wilhelm Leibniz Universität Hannover, 2020. http://d-nb.info/1205068325/34.

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10

Miller, John Richard Anthony. "Synthesis of optically active amino-acids and some chiral compounds as intermediates to squalestatin using novel organometallic catalysts and material from the chiral pool." Thesis, University of Essex, 1999. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.302567.

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11

Montagnon, T. "Synthetic studies towards the squalestatins." Thesis, University of Sussex, 2000. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.326933.

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12

Masters, Susannah Jane. "Studies towards the synthesis of the squalestatins." Thesis, University of Sheffield, 1999. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.298950.

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13

Barsanti, Paul Andrew. "Synthetic studies of the zaragozic acids/squalestatins." Thesis, University of Bath, 1996. https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.320429.

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14

Reid, Alison M. "Approaches to the core structure of the squalestatins." Thesis, Durham University, 1996. http://etheses.dur.ac.uk/5263/.

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The squalestatins are a new family of natural products which display potent cholesterol lowering effects. Common to all these natural products is the highly oxidised bicyclic core and the aim of this project was to achieve a concise synthetic route to this core unit. Initial studies were carried out using 2-benzyloxycyclohexanone as a model template. Following conversion to the 2-oxa-3-oxo-spiro<4.5>decan-6-one via addition of the dianion of 3-(para- tolylsulphonyl)propionic acid, coupling of a C(2) fragment was explored. Addition of carboethoxymethylenetriphenylphosphorane, followed by oxidation to the diol and protection as the acetonide led to the formation of 4- Ethoxycarbonyl-(2,2-dimethyl-5"-oxodispiro[perhydro[l,3]dioxolane-4,r- cyclohexane-2',2"-(5"-H-furan)]-5-yl. The alternative order of addition of the C(4) and C(2) units has also been undertaken. Manipulation of the ester group to a silyl ether afforded a less reactive functionality and C(4) was manipulated to allow for the coupling of the next fragment to form the spiro lactone. The addition of the dianion of 3-(parc-tolylsulphonyl)propionic acid to4-((^t)butyldimethylsilyloxymethyl)-2,2-dimethyl-l,3-dioxa-spiro<4.5>decan-6-one failed and another route to the spiro lactone was explored. Formation of 4 - ((^t)butyldimethy Isilyloxymethy l)-2,2-dimethyl-1,3,7-trioxa- dispiro<4.0.4.4>tetradecan-8-one (I) was achieved by allylation at C(4) followed by hydroboration of the double bond and subsequent oxidation. The C(l) side chain could be added to the spiro lactone using allyl magnesium bromide without compromising the other functionality present. Acid treatment of 4-((^t)butyldimethylsilyloxymethyl)-8-methoxy-2,2-dimethyl-8- propyl-l,3,7-trioxa-dispiro<4.0.4.4>tetradecane (II) promoted deprotection of the acetonide followed by concomitant cyclisation to the desired 6-hydroxy-9-propyl- 8,12-dioxatricyclo<7.2.1,0>dodec-7-yl-l-methanol (III). This showed the viability of the retrosynthetic analysis as a route to core analogues of the squalestatins. Studies to the fully substituted core were commenced using cis-cyclohexadiene diol. The diol was protected as its p-anisaldehyde acetal before the formation of the Diels Alder adduct (IV) using 4-phenyl-l,3,5-triazolinone. However a lack of time prevented its manipulation to the a-alkoxy ketone species through Lewis Acid mediated cleavage of the acetal. In a second retrosynthetic plan 2-benzyloxycyclohexanone was coupled with methyl tetronate prepared following the procedure of Pelter. Preliminary studies towards the addition of the C(l) side chain have been undertaken and initial results seem promising
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15

Roels, Jochen. "Beiträge zur Synthese von Modellsystemen des heterobicyclischen Grundgerüstes der Saragossasäuren/Squalestatine sowie methodische Untersuchungen zur chemoselektiven mono-Debenzylierung von N,N-Dibenzylaminen und katalytischen enantioselektiven Ringöffnung von meso-Epoxiden." Doctoral thesis, Saechsische Landesbibliothek- Staats- und Universitaetsbibliothek Dresden, 2000. http://nbn-resolving.de/urn:nbn:de:swb:14-994697037140-73077.

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Es wurden Untersuchungen zur Synthese von Modellsystemen des heterobicyclischen Grundgerüsts der Saragossasäuren/Squalestatine durch Acetalisierung unterschiedlich konfigurierter acyclischer Diketohexaole durchgeführt. In diesem Zusammenhang gelang die biderektionale Darstellung eines Modellsystems in sieben Stufen mit einer Gesamtausbeute von 34 %. Als Methode zur Etablierung der korrekten Konfiguration der Hydroxygruppen diente die asymmetrische Dihydroxylierung nach Sharples. In einem weiteren Teil der Arbeit wurde die selektive mono-Debenzylierung verschiedener N,N-Dibenzylamine mit Cer(IV)ammoniumnitrat (CAN) und DDQ untersucht. In diesem Kontext konnte eine neue, sehr schonende, Methodik zur chemoselektiven mono-Debenzylierung tertiärer N,N-Dibenzylamine erarbeitet werden. Im letzten Teil der Arbeit wurden zwei neue, verbrückte Heterobimetall-Katalysatoren auf Basis von BINOL-Liganden entwickelt. Diese Katalysatoren wurden für die asymmetrische Ringöffnung verschiedener meso-Epoxide mit 4-Methoxyphenol genutzt und lieferten die Öffnungsprodukte in guten Ausbeuten und Enantiomerenüberschüssen (ee: 80 - 90 %)
The intramolecular acetalisation of several diketohexaols tko the bicyclic skelleton of saragozic acids/squalestatines were investigated. It was possible, by using a bidirectional synthesis sequence, to obtain a model for the core structure of saragozic acids in seven steps with a total yield of 34 %. To establish the correct configuration of up to six hydroxygroups the Sharpless asymmetric dihydroxylation protocoll was used. In the second part of the dissertation a new and mild method for debenzylation of N,N- Dibenzylamines was elaborated. Tertiary amines incorporating two N-benzyl substituents are readily mono-debenzylated with CAN or DDQ. In the last part of the dissertation the synthesis of two bridged heterobimetallic catalysts for the catalytic enantioselective ring opening of meso-epoxides is described. The ring opening reaction was performed using 4-methoxyphenol as a nucleophile an different meso-epoxides to give the ring opened products in good yields and enaniomeric excesses (ee: 80 - 90 %)
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16

Roels, Jochen [Verfasser]. "Beiträge zur Synthese von Modellsystemen des heterobicyclischen Grundgerüstes der Saragossasäuren, Squalestatine sowie methodische Untersuchungen zur chemoselektiven Mono-Debenzylierung von N,N-Dibenzylaminen und katalytischen enantioselektiven Ringöffnung von Meso-Epoxiden / Jochen Roels." 2000. http://d-nb.info/962683213/34.

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