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Dissertations / Theses on the topic 'Natural products – Synthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 6 September 2023

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1

Azzouz, Mariam. "Enantioselective synthesis of natural products." Doctoral thesis, Universitat Rovira i Virgili, 2013. http://hdl.handle.net/10803/365571.

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El objetivo general del trabajo presentado es investigar nuevas metodologías para la síntesis de: a) nectrisina, un inhibidor de α-glucosidasas y α-mannosidasas, b) del fragmento oligosacarídico del antibiótico AT2433-A1, un antibiótico utilizado en el tratamiento de numerosos tipos de cánceres y, c) de análogos del cidofovir o HPMPC, nucleósido acíclico que incorpora una unidad de fosfonato, y que se utiliza en el tratamiento del citomegalovirus (CMV) en pacientes con SIDA. Síntesis enantioselectiva de nectrisina Retrosintéticamente la síntesis de la nectrisina puede llevarse a cabo po

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2

Zheng, Zehua. "Synthesis of bioactive natural products." Thesis, University of British Columbia, 2016. http://hdl.handle.net/2429/59815.

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Crude extracts of the rare macrofungus Serpula sp. collected from a wooded area in Sri Lanka showed antimicrobial activity. The novel fungal metabolite serpulanine (2.1) was isolated from the crude extract in very small amounts along with a number of additional secondary metabolites. In order to obtain sufficient quantities of serpulanine (2.1) for biological evaluation, a synthetic route was developed to the natural product and a small library of analogs that have been evaluated in a panel of bioassays. Serpulanine (2.1) inhibits the histone deacetylase I/II with a clear dose response curve.

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3

Kirkham, James E. D. "Synthesis of marine natural products." Thesis, University of Oxford, 2007. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.442593.

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4

Madden, Katrina Sophie. "Synthesis of polyene natural products." Thesis, Durham University, 2017. http://etheses.dur.ac.uk/12052/.

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A convergent approach was applied to the synthesis of a range of Xanthomonas pigments and a number of selected analogues, with a view to understanding more about their photoprotective properties, and utilising the group’s iterative Heck-Mizoroki/ iododeboronation cross-coupling methodology to access polyenyl intermediates. This involved the synthesis of a number of key arenyl building blocks. Three polyenyl building blocks were accessed via sequential Heck-Mizoroki and iododeboronation reactions, providing flexibility in the construction of the pigments and their analogues. Following some opti

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5

Guo, Haitao. "Synthesis of heteroaromatic natural products." [Ames, Iowa : Iowa State University], 2009.

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6

Simpson, Graham Bonar. "The synthesis of natural products." Thesis, Liverpool John Moores University, 2010. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.521739.

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7

Heaviside, Elizabeth Anne. "Analogues of antibacterial natural products." Thesis, University of Oxford, 2012. http://ora.ox.ac.uk/objects/uuid:6b5bd771-515b-49d0-8ec9-cee115d3aebf.

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Analogues of Antibacterial Natural Products Elizabeth Anne Heaviside, St Catherine’s College, University of Oxford DPhil Thesis, Trinity Term 2012 This thesis is concerned with the synthesis and biological evaluation of structural mimics for the natural products 16-methyloxazolomycin and lemonomycin which display potent biological activity including antibacterial and antitumour activity. Chapter 1 explores methods and approaches to the discovery of new antibacterial drugs and the challenges faced in this respect. It also gives an overview of the properties of the natural products investigated

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8

Hari, Taylor P. A. "Chemoenzymatic Synthesis of Polyketide Natural Products." Thesis, Université d'Ottawa / University of Ottawa, 2018. http://hdl.handle.net/10393/37220.

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Polyketide secondary metabolites constitute a structurally-diverse and clinically-important family of natural products. The wide range of biological activities represented by these substrates have contributed to therapeutic agents with annual sales exceeding $20B USD. Large multi-domain proteins called polyketide synthases (PKSs) use simple building blocks to generate highly-oxygenated and stereochemically-rich frameworks with astonishing selectivity. These substrates often feature rigidifying biases imposed by macrocyclic lactones and substituted heterocycles, which can impact their bioactive

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9

Mayweg, Alexander V. "Biomimetic synthesis of tropolone natural products." Thesis, University of Oxford, 2001. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.393410.

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10

Hookins, Daniel Ritchie. "Synthesis of oxygenated cyclohexene natural products." Thesis, University of York, 2011. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.547340.

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11

Jones, Nigel Alan. "Synthesis of carbohydrate-based natural products." Thesis, University of East Anglia, 2005. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.426420.

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12

Stein, Tobias. "Radical synthesis of quinazolinone natural products." Thesis, Loughborough University, 2007. https://dspace.lboro.ac.uk/2134/34389.

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Investigations into radical and palladium(0) cyclisations onto the C-2 position of the 3H-quinazolin-4-one moiety have been made. This has led to the syntheses of a number of biologically active quinazolinone natural products using alkyl, heteroaryl and acyl radical cyclisations. The reactions proceeded via a homolytic aromatic substitution mechanism. As such, fully rearomatised products were recovered. A C-2 radical 3H-quinazolin-4-one building block was also prepared. This turned out to have only limited synthetic applications. Radical cyclisations onto aryl groups were carried out using thi

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13

De, Silvestro Irene. "Total synthesis of phenolic natural products." Thesis, University of Edinburgh, 2017. http://hdl.handle.net/1842/29575.

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This thesis is regarded with the biomimetic total synthesis of phenolic natural products and describes two different projects. Chapter 1 introduces phenolic natural products, the most important biosynthetic pathways for their formation and some examples of relevant biomimetic syntheses. A short introduction to dimeric and pseudo-dimeric natural products can also be found in this chapter. Specific introductions can be found at the start of Chapters 2 and 3. Chapter 2 describes the total synthesis of a dimeric thymol derivative isolated from Arnica sachalinensis (which we have named “thymarnicol

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14

Lorente, Crivillé Adriana. "Marine Natural Products. Synthesis and structure determination." Doctoral thesis, Universitat de Barcelona, 2014. http://hdl.handle.net/10803/279367.

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Natural products from terrestrial plants and microorganisms have long been a traditional source of drugs. For centuries humans have been looking on their environment for medicines to treat illnesses. But unlike terrestrial sources, marine habitat has not been so extensively studied; this field awaited refinements in technologies to collect the source organisms, and development of more advanced analytic techniques to better understand the more complex isolated compounds. Since 1950s this field has suffered an exponential push; considering that water covers around a 70% of the earth’s surface, a

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15

Hyland, Christopher James Timothy. "Stereoselective Î³-lactam synthesis : methodology and natural products synthesis." Thesis, Imperial College London, 2003. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.410055.

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16

Wu, Boshen. "Synthesis of taurospongin A and other biologically active natural products." Thesis, University of Oxford, 2017. http://ora.ox.ac.uk/objects/uuid:37a34bc4-efb4-4a6b-9d44-a3ad1c8ae0be.

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This thesis firstly describes a synthesis of the natural product taurospongin A, a potent DNA polymerase beta inhibitor. Sharpless asymmetric dihydroxylation on olefin <b>E-1.60</b> followed by selective deoxygenation at C(2) via Barton‒McCombie reaction delivers the desired C(1)–C(10) carboxylic acid core. Subsequent esterification of the C(1)–C(10) fragment with C(1′)–C(25′) fatty acid furnishes the natural product in 13.5% yield. The structure of an unnamed natural product <b>2.14</b> isolated in 1974 is proven to be misassigned by previous studies within the Robertson group. As described i

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17

Malhi, B. S. "Synthetic studies related to natural products." Thesis, University of Newcastle Upon Tyne, 1988. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.381529.

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18

Murphy, Annabel Christine. "Structure Elucidation and Synthesis of Natural Products." Thesis, University of Canterbury. Chemistry, 2008. http://hdl.handle.net/10092/1748.

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In this thesis, synthetic chemistry was used as a tool in the exploration of various aspects of natural products discovered by the natural products research group at the University of Canterbury. Work on the constituent amino acids and connectivity of the pteratides, a potently cytotoxic series of cyclodepsipeptides, had been completed before the beginning of this work (carried out by Miss C. Chen). The elucidation of the stereochemistry of the constituent amino acids was undertaken in this present work. The synthesis of all stereochemical entities of a number of unusual amino acids, which wer

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19

Turkut, Engin. "Chemoenzymatic Synthesis Of Biologically Active Natural Products." Master's thesis, METU, 2004. http://etd.lib.metu.edu.tr/upload/12604854/index.pdf.

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Racemic metyhl 3-cyclohexene-1-carboxylate was resolved via enzymatic hydrolysis to afford the enantiomerically enriched 3-cyclohexene-1-carboxylic acid with PLE (S-configuration), HLE (S-configuration), CCL (S-configuration) and PPL (R-configuration) . The nucleoside&amp<br>#65533<br>s precursor, 5-(hydroxymethyl)-2-cyclohexen-1-ol (19), was synthesized by iodolactonization, followed by iodine elimination and the reduction of the lactone. In connection with this work, alpha,beta-unsaturated and saturated cyclic ketones were selectively oxidized on alpha&#039<br>- and alpha-positions using Mn

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20

Park, Jae Hyun. "Synthesis of Natural Products Containing Hydroxylated Pyrrolidines." Thesis, University of Auckland, 2002. http://hdl.handle.net/2292/1921.

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This thesis contains two parts. The first part describes the synthesis of orthogonally protected L-2,3-cis-3,4-trans-DHP 1.44 in eleven steps starting from L-arabinose via double displacement of bis-mesylate 2,8. The second part describes the synthesis of the spiroacetal fragment of the alkaloid broussonetine H. (±)-2-(3-Bromopropyl)-1,7-dioxaspiro[5.5]undecane (3.38) was prepared in nine steps from 1,4- butanediol (1.49), propargyl bromide (3.33) and δ-valerolactone (1.51). Enantioenriched material, namely (2S)-2-(3-bromopropyl)-1,7-dioxaspiro[5.5]undecane (4.2) was synthesized in thirteen st

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21

Bulger, Paul G. "Studies of the synthesis of natural products." Thesis, University of Oxford, 2003. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.289360.

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22

Twiddle, Steven John Robert. "The stereoselective synthesis of polyene natural products." Thesis, Durham University, 2005. http://etheses.dur.ac.uk/2771/.

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A strategy for the stereocontrolled synthesis of polyene units was developed which centred around the chemistry of the vinyl boronate ester 4,4,6-trimethyl-2-vinyl-l,3,2- dioxaborinane 123. Reaction conditions have been developed to allow the Heck coupling of 123 with a range of aryl and alkenyl electrophiles. The reaction is promoted by cationic palladium species which can be generated through the addition of metal salts to the reaction mixture. Conversely conditions have also been developed which allows 123 to react exclusively at the boron functionality along the Suzuki-Miyaura pathway, the

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23

Sutkowski, A. C. "The synthesis and biosynthesis of natural products." Thesis, Open University, 1988. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.380830.

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24

McAulay, Kirsten. "The total synthesis of furanocembrane natural products." Thesis, University of Glasgow, 2017. http://theses.gla.ac.uk/8448/.

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The furanocembranes are a family of marine diterpenoids isolated from octocoral invertebrates. These macrocyclic natural products possess interesting molecular structures including a furan ring at C3-C6 and a butenolide moiety encompassing C10-C12. As well as their unique structures, family members have shown promising biological activities, and thus they represent attractive synthetic targets. This thesis describes the synthetic efforts towards two of these family members: pukalide and 7-acetylsinumaxmol B. In particular, focus has been directed towards the investigation of different syntheti

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25

Pasqua, Adele Elisa. "Total synthesis of enamide-containing natural products." Thesis, University of Glasgow, 2013. http://theses.gla.ac.uk/4088/.

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Enamides are an important class of functional group commonly present in natural products and drug candidates. In particular, enamides and dienamides are common in many anti-parasitic and anti-cancer natural products and pharmaceutical drug leads. The enamide moiety is strictly related to the biological activity of such compounds as it is directly involved in their mode of action. Due to the great importance of the enamide moiety in biological and medicinal chemistry, a deep interest has risen in the synthetic community in the past two decades and a wide variety of methodologies for the prepara

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26

Hariprakasha, H. K. "Synthesis Of Natural Products Based On Cyclohexadienes." Thesis, Indian Institute of Science, 1996. https://etd.iisc.ac.in/handle/2005/118.

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The thesis entitled "Synthesis of Natural Products Based on Cyclohexadienes" consists of two chapters. Chapter 1 is divided into two parts. Part I gives a brief introduction to the structure, synthesis, biosynthesis and biological activities of some naturally occurring phthalides (eg. mycophenolic acid 1, zinniol2, phthalides 3 & 4). A general strategy for the preparation of highly substituted phthalides is also described. Cycloaddition of 1,s-dimethoxycoclohexa-1, 4-diene with dimethylacetylenedicarboxylate(DMAD) followed by an Alder-Rickert reaction gave the diester 5 which upon hydrolysis

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27

Hariprakasha, H. K. "Synthesis Of Natural Products Based On Cyclohexadienes." Thesis, Indian Institute of Science, 1996. http://hdl.handle.net/2005/118.

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The thesis entitled "Synthesis of Natural Products Based on Cyclohexadienes" consists of two chapters. Chapter 1 is divided into two parts. Part I gives a brief introduction to the structure, synthesis, biosynthesis and biological activities of some naturally occurring phthalides (eg. mycophenolic acid 1, zinniol2, phthalides 3 & 4). A general strategy for the preparation of highly substituted phthalides is also described. Cycloaddition of 1,s-dimethoxycoclohexa-1, 4-diene with dimethylacetylenedicarboxylate(DMAD) followed by an Alder-Rickert reaction gave the diester 5 which upon hydrolysis w

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28

Nimkar, Sandeep Krishnaji. "Studies in asymmetric synthesis: Development of new synthetic methods for syntheses of natural products." Diss., The University of Arizona, 1993. http://hdl.handle.net/10150/186538.

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The research, to be discussed in three chapters, involves the development of new synthetic methods which are applicable to the total synthesis of many natural products. Chapter 1: As a part of a program to synthesize new auxiliary agents for asymmetric synthesis, we have prepared a structurally rigid acetal from norbornene in three chemical steps. This enantiomerically pure acetal has been used for resolution of racemic α-hydroxy esters and might be applied as a chiral auxiliary for diastereoselective reactions. Chapter 2: The Calicheamicin and Esperamicin antibiotics have shown remarkable bio

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29

Dyson, Bryony Sara. "Determining the structures of halogenated marine natural products by total synthesis." Thesis, University of Oxford, 2011. http://ora.ox.ac.uk/objects/uuid:31737a99-a13c-4110-b36d-1c043b66565b.

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Elatenyne, a brominated C<sub>15</sub> acetogenin isolated from the red Laurencia elata marine algae, was originally assigned a pyranopyran structure. Previous total synthesis of the pyranopyran structure has found this assignment to be incorrect. During this work the revised 2,2’-bifuranyl skeleton of elatenyne was suggested, but this skeleton has 32 possible diastereomers. The most likely diastereomer of elatenyne was predicted using computational <sup>13</sup>C NMR chemical shift calculation in combination with the possible stereochemical outcomes from the proposed biosynthesis. Chapter 1 i

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30

Sanderson, Adam Jan. "Synthesis of chiral natural products from citric acid." Thesis, University of Salford, 2001. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.366315.

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31

Andrew, R. G. "Synthetic studies on aaptamine and related natural products." Thesis, University of Cambridge, 1986. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.383699.

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32

Elend, D. L. "Asymmetric Baylis-Hillman products." Thesis, University of Oxford, 2002. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.249263.

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33

Giltrap, Andrew M. "Total Synthesis of Natural Products with Antimicrobial Activity." Thesis, The University of Sydney, 2017. http://hdl.handle.net/2123/17195.

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Natural products are an essential source of many modern medicines. Examples of important natural products include the antibiotic penicillin and the antimalarial quinine. One significant class of bioactive natural products are non-ribosomal peptides (NRPs) and two prototypical members of this class are the extremely important antibiotics, penicillin and vancomycin. Currently, bacterial resistance to antibiotics is one of the most pressing global health issues. The need for new antibiotics with novel mechanisms of action is paramount. This thesis describes the total synthesis of the recently iso

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34

Sheth, Ritesh B. "Development of new synthetic methodologies and the synthesis of natural products." Access to citation, abstract and download form provided by ProQuest Information and Learning Company; downloadable PDF file, 101 p, 2010. http://proquest.umi.com/pqdweb?did=1993336351&sid=2&Fmt=2&clientId=8331&RQT=309&VName=PQD.

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35

Lejeune, Guillaume. "Photochemical studies toward the synthesis of natural products." Doctoral thesis, Universitat Autònoma de Barcelona, 2015. http://hdl.handle.net/10803/314573.

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Els derivats de ciclobutà son uns compostos remarcables no nomes com productes naturals, com el en camp de les feromones on moltes estructures contenen un ciclobutà, però també alguns ciclobutans juguen un paper molt important en l’àrea farmacèutica, com en el cas de molts anàlegs de nucleòsid que tenen una gran activitat contra la replicació d’alguns virus (Herpès o VIH). La fotoquímica en síntesi orgànica ha proporcionat un mètode extremadament potent per la conversió de substrats senzills a productes més complexos. Diverses dificultats van associar amb l'actuació de les fotoreaccions en l'

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36

Mohammadi, Ziarani Ghodsi. "Enantioselective synthesis of natural products via enzymatic desymmetrizations." Thesis, National Library of Canada = Bibliothèque nationale du Canada, 2000. http://www.collectionscanada.ca/obj/s4/f2/dsk1/tape3/PQDD_0018/NQ54023.pdf.

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37

Clark, J. Stephen. "Approaches to the synthesis of oxocane natural products." Thesis, University of Cambridge, 1988. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.293810.

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38

Moses, John E. "Studies towards the biomimetic synthesis of natural products." Thesis, University of Oxford, 2004. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.409116.

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39

Choudhury, Abdul K. "Synthesis of the acylpyridones : natural and unnatural products." Thesis, Loughborough University, 2010. https://dspace.lboro.ac.uk/2134/6310.

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The 3-acyl-4-hydroxy-pyridin-2-one core is a common feature observed in a number of natural products. This thesis describes the design and the development of an isoxazolopyridone as a masked form of this core and elaboration at the sites C-3 (Me), C-7 and N-5 of the related isoxazolopyridone. The polar nature of the heterocyclic trione makes these compounds difficult to work with, particularly with regards to purification and handling. A strategy is applied to disguise this polar nature, by masking the 4-hydroxy and 3-acyl functions as an isoxazole. The isoxazolopyridone building block is avai

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40

Lucas, Catherine Louise. "Synthesis of prenylated natural products utilising pericyclic processes." Thesis, University of Nottingham, 2011. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.555739.

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This Thesis describes the synthesis of prenylated phenolic natural products using pericyclic reactions, including the aromatic Claisen rearrangement and 67t- electrocyclisations. Chapter 1 presents an overview of the biological processes responsible for the generation of prenylating agents in Nature and the construction of prenylated phenolic compounds by the convergence of biosynthetic pathways. This is followed by a synopsis of established methods to access prenylated phenols in the laboratory. Chapter 2 focuses on the use of the aromatic Claisen rearrangement to construct prenylated phenols

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41

Kelly, Michael James. "Stereoselective synthesis of novel natural products from carbohydrates." Thesis, University of Exeter, 1990. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.385726.

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42

Newman, Nicola Ann. "Cyclisation strategies towards the synthesis of natural products." Thesis, University of Southampton, 2000. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.342637.

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43

Leslie, Pauline. "Studies towards the synthesis of chlorinated natural products." Thesis, University of Bristol, 2003. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.268989.

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44

Warrellow, Graham John. "Synthesis of natural and unnatural products from azidocinnamates." Thesis, Imperial College London, 1990. http://hdl.handle.net/10044/1/46602.

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Barrett, Tim Nicholas. "Biomimetic synthesis of resorcylates natural products and analogues." Thesis, Imperial College London, 2015. http://hdl.handle.net/10044/1/50293.

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The resorcylate unit (2, 4-dihydroxybenzoic acid) is found in numerous biologically active natural products. This thesis outlines the application of a novel biomimetic synthesis strategy to the syntheses of resorcylate natural products and analogues. A synthetic pathway to the meroterpenoid antibiotic Hongoquercin B has been successfully developed in nine steps from trans, trans-farnesyl acetate using a double biomimetic strategy. A regioselective decarboxylative farnesyl migration and cycloaromatisation gave the resorcylate, which undergoes a lewis acid mediated diastereoselective cationic ep

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46

Bunga, Flora. "Synthesis of cyclic peptide natural products and peptidomimetics." Thesis, University of Bath, 2015. https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.675730.

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Chitin, a linear polymer of N-acetylglucosamine, is an essential structural component of fungal, nematode and insect pathogens but is not found in human physiology. Chitinases, which hydrolyze this polymer, play a key role in life cycle of these pathogens and associated pathogenesis. Consequently chitinase inhibitors have generated a lot of interest given their potential as insectides, fungicides and antimalarials. Herein, approaches are reported to the synthesis of some non-sugar based chitinase inhibitors: the cyclic pentapeptide natural products argifin, banyasin A and diketopiperazines rel

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47

Mahaney, Paige E. (Paige Erin). "Efforts toward the synthesis of taxane natural products." Thesis, Massachusetts Institute of Technology, 1996. http://hdl.handle.net/1721.1/38760.

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48

Blunt, Christoper Edward. "The synthesis of benzisothiazole and benzothiazole natural products." Thesis, University of Nottingham, 2018. http://eprints.nottingham.ac.uk/49541/.

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Chapter 1 gives an introduction to benzisothiazole and benzothiazole natural products. It explores the scope of natural products that are known within these families and discusses what they are used for, how they have been made and how they may have been biosynthesised. Chapter 1 provides a review of each family of natural products in turn. Chapter 2 describes the total synthesis of the benzisothiazole natural products aulosirazole and pronqodine A, and a series of unnatural analogues. The Chapter begins with a short discussion on the use of the Diels-Alder reaction for the formation of naphth

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49

Kostiuk, Sarah Louise. "The total synthesis of macrocyclic bisbibenzyl natural products." Thesis, University of Southampton, 2009. https://eprints.soton.ac.uk/193731/.

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This thesis is concerned with the total synthesis of two related macrocyclic natural products, cavicularin and riccardin C. Cavicularin is particularly noteworthy owing to its interesting structure: its 14-membered macrocyclic core imparts sufficient strain on the system to force one of the arenes in this paracycophane to adopt a boat-shaped conformation, deviating from planarity. The natural product also exhibits optical activity despite containing no chiral centres, this being due to axial and planar chirality in the molecule. Herein, routes to these two natural products are presented. Key s

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50

Nolan, William Peter. "Synthesis of indolo[2,3-A]carbazole natural products." Thesis, University of Cambridge, 1990. https://www.repository.cam.ac.uk/handle/1810/272982.

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