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Dissertations / Theses on the topic 'Taxol - Synthesis'

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Published: 4 June 2021

Last updated: 6 September 2023

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1

Rodriguez, Patricia Fernandez. "Streamlined synthesis of taxol analogues." Thesis, University of Oxford, 2017. https://ora.ox.ac.uk/objects/uuid:58d4a7f3-038e-4c4a-9aec-67267277670f.

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This thesis centres on the synthesis of taxol analogues via late-stage hydroxylation with P450 enzymes. To accomplish this, the taxane core, specifically taxa-4(5),11(12)-dien-2-one, was synthesised by classical synthetic methods, and subsequently oxidised using P450<sub>BM3</sub> mutants. Chapter 1 introduces enzymatic catalysis, and the advantages and disadvantages of its application to organic synthesis. Additionally, an overview of taxol, including its discovery, mode of action, biosynthesis and large-scale production, and a summary of the previously reported approaches to the taxane core

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2

Kreilein, Matthew M. "Progress toward the total synthesis of paclitaxel (taxol)." The Ohio State University, 2005. http://rave.ohiolink.edu/etdc/view?acc_num=osu1117063322.

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3

Hofferberth, John E. "Progress toward the total synthesis of Taxol /." The Ohio State University, 2002. http://rave.ohiolink.edu/etdc/view?acc_num=osu1486463321625038.

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4

Tierney, Jason P. "Stereoselective synthesis of C-glycosidic oxetanes." Thesis, Imperial College London, 1995. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.309528.

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5

Metaferia, Belhu B. "Synthesis of Taxol™ Analogs as Conformational Probes." Diss., Virginia Tech, 2002. http://hdl.handle.net/10919/28428.

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Taxol™, isolated from the bark of Taxus brevifolia in the late 1960s, and the semisynthetic analog Taxotere™ have proven clinical importance for the treatment of ovarian and breast cancer. Taxol™ exerts its biological effect by binding to polymerized tubulin and stabilizing the resulting microtubules. Studies aimed at understanding the biologically active conformation of taxol and its binding environment on β-tubulin are described. This knowledge is important because it could lead to the design of structurally less complicated drugs with better efficacy and better bioavailability. Moreover

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6

Zeng, Qingbei. "Studies toward the total synthesis of Taxol®/." The Ohio State University, 1999. http://rave.ohiolink.edu/etdc/view?acc_num=osu1488190595940418.

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7

Wilkes, Antonia. "Towards the synthesis of the ABC tricycle of Taxol." Thesis, University of Glasgow, 2015. http://theses.gla.ac.uk/5885/.

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Taxol is one of the world’s most successful drugs used in the treatment of cancers. Isolated from the bark of the Pacific yew tree (Taxus brevifolia), it is a molecule of great interest within organic chemistry; with six total syntheses and a number of synthetic works having been published since its discovery. A semi-convergent synthesis of an intermediate in Holton’s synthesis was planned. The overall synthetic plan is shown below. The A ring would be installed by an intramolecular pinacol condensation. The BC bicycle would be closed by ring-closing metathesis at C10-C11. The ketone at C12 wo

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8

Baloglu, Erkan Jr. "A New Synthesis of Taxol®, from Baccatin III." Thesis, Virginia Tech, 1998. http://hdl.handle.net/10919/36930.

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Taxol®, an important anticancer drug, was first isolated in extremely low yield from the bark of the western yew, Taxus brevifolia. The clinical utility of Taxol has prompted a tremendous effort to obtain this complex molecule synthetically. Due to the chemical complexity of Taxol, its commercial production by total synthesis is not likely to be economical. Another natural product, 10-deacetyl baccatin III, is readily available in higher yield. Several methods have been reported for the synthesis of Taxol by coupling baccatin III and the N-benzoyl-β-phenylisoserine side chain. A new method

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9

Tsui, Hon-Chung. "Studies on the synthesis of Kaurane Diterpenoids and Taxol /." The Ohio State University, 1998. http://rave.ohiolink.edu/etdc/view?acc_num=osu1487951214937412.

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10

Letort, Aurelien. "Ring-closing metathesis cascade toward a formal synthesis of taxol." Thesis, University of Glasgow, 2015. http://theses.gla.ac.uk/6677/.

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TaxolTM and its derivatives are the largest selling anticancer drugs of all time. Numerous synthetic works and total syntheses have been published since its discovery, but to date no high yielding synthesis with less than 37 steps has been achieved. In this thesis is presented our synthetic efforts toward such a robust and efficient synthesis of Taxol. The optimisation of the Shapiro coupling fragments syntheses were investigated to enhance the robustness of our strategy. Then the C7-deoxy model ABC tricycle ring-system of Taxol, which lacks the oxygenated substituent at C7, has been efficient

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11

Koo, Ki Chul. "Studies towards the total synthesis of 1-deoxy-8-demethyl taxol." Tallahassee, Florida : Florida State University, 2009. http://etd.lib.fsu.edu/theses/available/etd-08222009-032151/.

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Thesis (Ph. D.)--Florida State University, 2009.<br>Advisor: Robert A. Holton, Florida State University, College of Arts and Sciences, Dept. of Chemistry and Biochemistry. Title and description from dissertation home page (viewed on April 27, 2010). Document formatted into pages; contains xvii, 362 pages. Includes bibliographical references.

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12

Parra, Stephanie Marie. "A double Diels-Alder strategy towards the synthesis of Taxol analogues." Thesis, National Library of Canada = Bibliothèque nationale du Canada, 2001. http://www.collectionscanada.ca/obj/s4/f2/dsk3/ftp05/NQ66181.pdf.

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13

Lian, Yiqian. "Chromium and iron organometallics in organic synthesis synthetic studies toward total synthesis of taxol and chromium to iron transfer processes /." Diss., Connect to online resource - MSU authorized users, 2006.

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14

Hodge, Mathis. "Synthesis and Antiproliferative Activity of C3' and B-ring Modified Paclitaxel Analogs." Thesis, Virginia Tech, 2007. http://hdl.handle.net/10919/30940.

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The natural product, paclitaxel, has made tremendous contributions in supplying the arsenal of anticancer therapeutics, and was FDA approved for clinical use in 1992. In order to design simplified analogs, the conformation that paclitaxel adopts when binding to tubulin has been the subject of ongoing studies. Much evidence has led to a T-taxol proposal and a C3' constrained analog has been designed and synthesized as a test of this conformation. In the search for more active analogs, a number of modifications have been made to paclitaxel by other researchers. However, the nature of the alterat

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15

Chen, Ru. "Isolation, structure elucidation and approaches to the partial synthesis of new taxol analogs." Thesis, This resource online, 1994. http://scholar.lib.vt.edu/theses/available/etd-11102009-020316/.

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16

Guerot, Carine. "Construction of carbocycles via oxonium ylides generation and rearrangement : towards the synthesis of taxol." Thesis, University of Glasgow, 2009. http://theses.gla.ac.uk/645/.

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The diterpenoid natural product Taxol, first discovered in the late 1960’s, is one of the most important current drugs for the treatment of several cancers including breast and ovarian cancers. Although tremendous efforts towards its synthesis have been made in the last two decades, resulting in six elegant total syntheses, Taxol still constitutes a remarkable challenge for organic chemists due to its unique structural framework. The high level of interest has spilled over to our laboratory, the purpose of this thesis was to develop an approach for the construction of medium-ring fused polycar

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17

Baloglu, Erkan. "Synthesis and Biological Evaluation of Paclitaxel Analogs." Diss., Virginia Tech, 2001. http://hdl.handle.net/10919/27853.

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The complex natural product paclitaxel (TaxolÂ®), first isolated from Taxus brevifolia, is a member of a large family of taxane diterpenoids. Paclitaxel is extensively used for the treatment of solid tumors, particularly those of the breasts and ovaries. In order to obtain additional information about the mechanism of action of paclitaxel and the environment of the paclitaxel-binding site, several fluorescent analogs of paclitaxel were synthesized, and their biological activities have been evaluated. For the investigation of possible synergistic effects, concurrent modifications on sele

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18

Magnus, Nicholas Andrew. "Synthesis of the anthraquinone portion of dynemicin A : Taxanes chiral construction of the A, B and C rings of taxol." Thesis, University of Bristol, 1996. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.319045.

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19

Naylor, Guy James. "Studies of novel anticancer agents : progress towards leiodermatolide and the total synthesis of analogues and hybrids of dictyostatin, discodermolide and taxol." Thesis, University of Cambridge, 2011. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.609305.

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20

Jost, Sylvie. "Nouvelles stratégies pour la synthèse des chaines latérales du Taxol(R)(paclitaxel) et du Taxotère(R)(docétaxel) : couplage imine, aldéhyde et couplage nitrone, acétal de cétène." Université Joseph Fourier (Grenoble), 1996. http://www.theses.fr/1996GRE10265.

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Le taxol# et le taxotere# sont deux composes anticancereux parmi les plus efficaces a l'heure actuelle. L'hemisynthese est actuellement la methode de choix pour preparer ces deux molecules. Elle fait intervenir un precurseur naturel abondant dont l'extraction des feuilles d'ifs est sans danger pour l'espece, et une chaine laterale synthetique. Les travaux de notre laboratoire, orientes principalement vers la recherche de nouvelles strategies de synthese de ces chaines laterales syn (2r,3s), ont montre qu'il etait possible de realiser l'esterification entre le precurseur naturel et une chaine s

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21

Lane, Charlotte Alice Louise. "Synthetic studies towards taxol." Thesis, Imperial College London, 1997. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.267854.

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22

Lam, Polo Chun Hung. "Experimental and Computational Studies in Bioorganic and Synthetic Organic Chemistry." Diss., Virginia Tech, 2004. http://hdl.handle.net/10919/40013.

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Cationâ Ï interaction is an important determinant in protein structure and function. Among the three proteinogenic aromatic amino acids, tryptophan (Trp) is the strongest cationâ Ï donor. We reported the asymmetric syntheses of tryptophan regioisomers in which the amino acid side chain is attached at different position of the indole moiety. These new tryptophan regioisomers can effect a different mode of cationâ Ï interaction. In nature, dramatic increases in binding affinity can be achieved through multivalent binding. Following a fragmentation-dimerization approach, we synthesized

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23

Liu, Changhui. "Syntheses and Bioactivities of Targeted and Conformationally Restrained Taxol Analogs." Diss., Virginia Tech, 2004. http://hdl.handle.net/10919/11186.

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Taxol (1) was first isolated from the bark of the Pacific yew about 35 years ago by Drs. Wall and Wani. Although its development as an anticancer agent was delayed by numerous reasons, including its scarcity and insolubility, the discovery of its tubulin-assembly activity and other factors motivated oncologists to overcome these problems. It has since become one of the most important current drugs for the treatment of several cancers, including breast and ovarian cancers. Like almost all anticancer drugs taxol does have some toxic side effects and many tumors also show significant resistance

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24

Elmore, Steven W. "Synthetic studies en route to taxol /." The Ohio State University, 1993. http://rave.ohiolink.edu/etdc/view?acc_num=osu1487847761307427.

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25

FERREIRA, JEAN-PAUL. "Synthese convergente du squelette taxoide tetramethyltricyclo (9. 3. 1. 0. 3,8) pentadecane (doctorat : pharmacochimie)." Paris 11, 1998. http://www.theses.fr/1998PA114809.

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26

Yang, Chao. "Syntheses and Bioactivities of Targeted and Conformationally Restrained Paclitaxel and Discodermolide Analogs." Diss., Virginia Tech, 2008. http://hdl.handle.net/10919/28942.

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Paclitaxel was isolated from the bark of <i>Taxus brevifolia</i> in the late 1960s. It exerts its biological effect by promoting tubulin polymerization and stabilizing the resulting microtubules. Paclitaxel has become one of the most important current drugs for the treatment of breast and ovarian cancers. Studies aimed at understanding the biologically active conformation of paclitaxel bound on β–tubulin are described. In this work, the synthesis of isotopically labeled taxol analogs is described and the REDOR studies of this compound complexed to tubulin agrees with the hypothesis that palic

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27

MULLER, BENOIT. "Contribution a la synthese totale du taxol." Palaiseau, Ecole polytechnique, 1996. http://www.theses.fr/1996EPXX0018.

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Le taxol est un diterpene de la famille des taxanes et possede une activite anticancereuse importante avec un mode d'action original. L'objectif de ce travail de these a ete de developper une approche de synthese totale du taxol, fondee sur une strategie convergente de type acabc faisant intervenir une fermeture tardive du cycle b en position c9-c10. Dans une premiere partie, toute une gamme de synthons correspondant au cycle a a ete synthetisee de facon originale en utilisant de nombreux aspects de la chimie de l'etain. A partir des differents synthons ainsi elabores, une serie d'etudes explo

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28

GUIR, FREDERIC. "Contribution a la synthese totale du taxol." Paris 11, 1990. http://www.theses.fr/1990PA112038.

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Ce travail se divise en deux parties: la premiere partie s'attache a l'etude de la formation des cycles b et c du taxane sur un modele ainsi que de la stereochimie de la jonction de ces cycles b/c par voie photochimique. Le produit final obtenu: la 14,14-dimethyl-tricyclo 9. 2. 1. 0#3#,#8 tetradecanedione-2,10 possede la jonction de cycle trans 3,8 inverse de celle du taxane. La deuxieme partie decrit la synthese de la dihydroxy-2,12 trimethyl-4,8,11 tricyclo 5. 3. 1. 1#4#,#1#1 dodecene-8 one-5 qui par retroaldolisation conduirait a la formation du systeme bicyclo 5. 3. 1 undecene a/b du taxol

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29

Payne, Lloyd James. "Synthetic studies towards selected natural products." Thesis, University of Sussex, 1997. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.388677.

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30

Jitrangsri, Chote. "Approaches to the synthesis of modified taxols." Diss., Virginia Polytechnic Institute and State University, 1986. http://hdl.handle.net/10919/49801.

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31

Johnston, Jeffrey N. "Synthetic studies directed toward polycavernoside A and Taxol(RTM) (paclitaxel) /." The Ohio State University, 1997. http://rave.ohiolink.edu/etdc/view?acc_num=osu1487946103569429.

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32

Chavan, S. P. "Synthetic studies towards taxol and development of synthetically useful methodology." Thesis(Ph.D.), CSIR-National Chemical Laboratory, Pune, 2006. http://dspace.ncl.res.in:8080/xmlui/handle/20.500.12252/2790.

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33

Mitchell, William Peter. "Stereoselective synthesis of the TaxolÂ®A--ring." Thesis, Imperial College London, 2003. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.405558.

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34

MARTEL, JEAN-PHILIPPE. "Etude de nouvelles approches de la synthese total du taxol." Université Louis Pasteur (Strasbourg) (1971-2008), 1994. http://www.theses.fr/1994STR13164.

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Le taxol est une molecule d'un grand interet pharmacologique. Nous nous sommes interesses a la synthese totale de ce produit naturel, en developpant successivement deux strategies, dans le but notamment de construire le cycle b a huit atomes de carbone. La premiere strategie est basee sur une transposition de type wagner-meerwein d'un systeme bicyclique 7/7 pour conduire a un systeme bicyclique 6/8 correspondant aux cycles a et b du taxol. Plusieurs precurseurs potentiels pour cette transposition ont ete synthetises puis testes. Cette approche n'a pas donne les resultats escomptes et n'a pas e

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35

Saravanan, K. "Synthetic studies towards taxol and synthetic methodologies using π-facial stereoselection and phosphacumulene ylides". Thesis(Ph.D.), CSIR-National Chemical Laboratory, Pune, 1998. http://dspace.ncl.res.in:8080/xmlui/handle/20.500.12252/3368.

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36

Yuan, Haiqing Jr. "Studies on the Chemistry of Paclitaxel." Diss., Virginia Tech, 1998. http://hdl.handle.net/10919/30671.

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Paclitaxel is a natural occurring diterpene alkaloid originally isolated from the bark of Taxus brevifolia. It is now one of the most important chemotherapeutic agents for clinical treatment of ovarian and breast cancers. Recent clinical trials have also shown paclitaxel's potential for the treatment of non-small-cell lung cancer, head and neck cancer, and other types of cancers. While tremendous chemical research efforts have been made in the past years, which established the fundamental structure-activity relationships of the paclitaxel molecule, and provided analogs for biochemical studies

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37

KERKAR, BRAHIM. "Contribution a la synthese totale du taxol et de ses analogues a la recherche de nouvelles molecules anticancereuses (doctorat : pharmacochimie)." Paris 11, 1998. http://www.theses.fr/1998PA114814.

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38

Zhao, Jielu. "Design, Syntheses and Biological Activities of Paclitaxel Analogs." Diss., Virginia Tech, 2011. http://hdl.handle.net/10919/77272.

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The conformation of paclitaxel in the bound state on the protein has been proposed to be the T-taxol conformation, and paclitaxel analogs constrained to the T-taxol conformation proved to be significantly more active than paclitaxel in both cytotoxicity and tubulin polymerization assays, thus validating the T-taxol conformation as the tubulin-binding conformation. In this work, eight compounds containing an aza-tricyclic moiety as a mimic of the baccatin core of paclitaxel have been designed and synthesized as water-soluble simplified paclitaxel analogs, among which 3.50-3.52 and 3.55 were con

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39

MAUGEIN, NATHALIE. "Contribution a la synthese totale du taxol acces a un modele du motif undecenoique des taxoides." Université Louis Pasteur (Strasbourg) (1971-2008), 1997. http://www.theses.fr/1997STR13026.

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Le taxol, extrait de l'if du pacifique est un diterpene de structure complexe qui presente une activite anticancereuse en agissant de maniere specifique comme poison du fuseau. Le theme essentiel de ce travail de these porte principalement sur le developpement d'une nouvelle strategie de synthese totale du taxol. Deux approches differentes ont ete etudiees. La premiere strategie envisagee, de type convergente (a+c ac abc) s'appuie sur une fermeture du cycle b du taxol en c8-c9 qui est fondee sur une cycloaddition intramoleculaire 3+2 d'un oxyde de nitrile sur une double liaison. Les etudes pre

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40

ALCARAZ, LILIAN. "Approche a la synthese totale des taxoides. Synthese dl cycle a du taxo." Université Louis Pasteur (Strasbourg) (1971-2008), 1995. http://www.theses.fr/1995STR13174.

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La structure complexe et hautement fonctionnalisee du taxol, ainsi que ses proprietes biologiques importantes, nous ont amene a proposer une nouvelle voie de synthese. Elle repose sur une double cycloaddition intramoleculaire 3+2 d'oxydes de nitrile sur des olefines. L'originalite de cette approche repose sur la mise en place simultanee des fonctions importantes et des trois cycles des taxanes a partir d'un intermediaire synthetique facile d'acces. Dans un premier temps, la synthese chirale du cycle a totalement fonctionnalise a ete effectuee. Nous avons mis au point une cyclisation biomimetiq

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41

GUO, YUPING. "Synthese du 11,11-dimethyl bicyclo 5. 3. 1 undec-3,8-diene, sous-structure a/b du taxol." Paris 11, 1992. http://www.theses.fr/1992PA112206.

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Ce travail se divise en deux parties et a pour but l'elaboration des cycles a et b du taxol 5, une substance naturelle aux proprietes antitumorales. Nos efforts ont ete concentres sur l'etude des fragmentations regioselectives de la liaison c4-c12 de 4,8,11-trimethyl-5-methoxy-12-oxo-2,5-epoxytricyclo 5. 31#4#,#1#1 dodecene-8 39, ouvrant une nouvelle voie d'acces aux derives du taxol. La premiere partie decrit les differentes tentatives d'agrandissement de cycle par fragmentations heterolytiques, via la reaction de haller-bauer, le systeme base-solvant: ko-t-bu/h#2o-dmso et la reaction de grob

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42

Qi, Jun. "Design, Syntheses and Bioactivities of Androgen Receptor Targeted Taxane Analogs, Simplified Fluorescently Labeled Discodermolide Analogs, and Conformationally Constrained Discodermolide Analogs." Diss., Virginia Tech, 2010. http://hdl.handle.net/10919/37537.

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Prostate cancer is the most common non-skin cancer for men in America. The androgen receptor exerts transcriptional activity and plays an important role for the proliferation of prostate cancer cells. Androgen receptor ligands bind the androgen receptor and inhibit its transcriptional activity effectively. However, prostate cancer can progress to hormone refractory prostate cancer (HRPC) to avoid this effect. Chemotherapies are currently the primary treatments for HRPC. Unfortunately, none of the available chemotherapies are curative. Among them, paclitaxel and docetaxel are two of the most ef

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43

Lawlor, Michael David. "New methodology for the generation and cycloadditions of thio-substituted ketenes ; A synthetic approach to the taxol A-ring." Thesis, Massachusetts Institute of Technology, 1997. http://hdl.handle.net/1721.1/10431.

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44

來俊吉. "The Total Synthesis of Taxol: Synthesis of Ring-A Intermediate." Thesis, 1997. http://ndltd.ncl.edu.tw/handle/76996687810792968184.

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碩士<br>中原大學<br>化學學系<br>85<br>The strategy used in our laboratory to synthesize diterpene natural compound-Taxol ( fig. 1-1 ) is a convergent approach. By synthesizing ring A and ring C with latent functions separately, followed by the coupling of ring A and ring C to form ring B and succeed the construction of the back bond structure of the target molecule. Together with the elaboration of the necessary functional groups with the correct stereochemistry the Taxol molecule could then be synthesized. This dissertation describes the preparation of Ring A intermediate ( fig.A ) which will be

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45

Chaing, Shu-Ming, and 蔣樹銘. "The Total Synthesis of Taxol: Synthesis of Ring-C Intermediate." Thesis, 1999. http://ndltd.ncl.edu.tw/handle/27999276963067700103.

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碩士<br>國立東華大學<br>化學研究所<br>87<br>The strategy used in our laboratory to synthesize diterpene natural compound-Taxol is that by synthesizing ring A and ring C with latent functions separately, followed by the coupling of ring A and ring C to form ring B and succeed the construction of the back bond structure of the target molecule. Together with the elaboration of the necessary functional groups with the correct stereochemistry the Taxol molecule could then be synthesized. This dissertation describes the preparation of Ring C intermidiate which will be used in the total synthesis of Ta

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46

"Synthesis of pseudo-AB ring analogues of taxol." 2003. http://library.cuhk.edu.hk/record=b6073595.

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Lee Chi-man.<br>"July 2003."<br>Thesis (Ph.D.)--Chinese University of Hong Kong, 2003.<br>Electronic reproduction. Hong Kong : Chinese University of Hong Kong, [2012] System requirements: Adobe Acrobat Reader. Available via World Wide Web.<br>Mode of access: World Wide Web.<br>Abstracts in English and Chinese.

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47

Allison, Jeffrey Corbin. "Studies directed towards the total synthesis of the natural product Taxol." 2003. http://wwwlib.umi.com/cr/utexas/fullcit?p3119656.

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48

Luu, Chii Huey, and 魯啟慧. "THE STUDY OF TOTAL SYNTHESIS TOWARD THE TAXOL C RING." Thesis, 1996. http://ndltd.ncl.edu.tw/handle/02567729095623590635.

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49

Joud, Carol Holton Robert Anthony. "Towards a new pathway for synthesis of taxol and its analogs." Diss., 2005. http://etd.lib.fsu.edu/theses/available/etd-11152005-144557.

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Thesis (M.S.)--Florida State University, 2005.<br>Advisor: Robert A. Holton, Florida State University, College of Arts and Sciences, Dept. of Chemistry. Title and description from dissertation home page (viewed Jan. 26, 2006). Document formatted into pages; contains xii, 196 pages. Includes bibliographical references.

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50

Zakharyan, Tatiana Yurievna. "Synthesis and biological studies of a fullerene-Taxol conjugate and fullerene-based transfection vectors." Thesis, 2006. http://hdl.handle.net/1911/19003.

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Fullerene (C60) derivatives have been extensively studied for a variety of medical applications, which include neuroprotective agents, HIV-1 protease inhibitors, photosensitizers for photodynamic therapy, MRI contrast agents, and radiopharmaceuticals. The first part of this work is dedicated to the development of a new application of C60 as a slow-release system for the liposome aerosol delivery of lipophilic chemotherapeutics to lung cancer. TaxolRTM (paclitaxel), one of the most active anticancer drugs in clinical use, has shown significant potential for treatment of lung cancer when deliver

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