Dissertations / Theses on the topic 'Mitsunobu reaction'
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Camp, David. "Some Aspects of the Mitsunobu Reaction." Thesis, Griffith University, 1990. http://hdl.handle.net/10072/366203.
Full textThesis (PhD Doctorate)
Doctor of Philosophy (PhD)
Division of Science and Technology
Science, Environment, Engineering and Technology
Full Text
Shannon-Little, Andrew Laurence. "Studies towards a phosphorus(V)-catalysed Mitsunobu reaction." Thesis, University of Nottingham, 2016. http://eprints.nottingham.ac.uk/33038/.
Full textFu, Jiasheng. "Investigation of stereoselection by the Mitsunobu reaction and modification of the Hendrickson reaction." Thesis, National Library of Canada = Bibliothèque nationale du Canada, 2000. http://www.collectionscanada.ca/obj/s4/f2/dsk1/tape2/PQDD_0009/NQ59960.pdf.
Full textBell, Kathryn Emma. "Advances in the retro-Cope elimination." Thesis, University of Nottingham, 1996. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.307744.
Full textFelten, Anne-Sophie. "Synthèse de N-aminopeptides. Application à la synthèse de nouveaux foldamères." Thesis, Vandoeuvre-les-Nancy, INPL, 2007. http://www.theses.fr/2007INPL095N/document.
Full textThis work describes the synthesis, the oligomerization and the structural study of N-aminopeptides. By extrapolating an original strategy of hydrazinoacids synthesis developed in the LCPM we were able to obtain N-aminodipeptides in high optical purity in a satisfactory way. These compounds were the indispensable precursors in order to continue the project. We were able to show that the activation of the acidic partner involved in the key reaction of Mitsunobu usually obtained by the use of the phtalimide group, could be advantageously realized by the introduction of a hydrazone moiety with strong electron-withdrawing character. An extension of this method on solid support is a result which constitutes an effective application of a Mitsunobu protocol in Solid Phase Organic Chemistry. The Naminodipeptides thus obtained were studied in reactions of oligomérisation. A preliminary study in liquid phase allowed to demonstrate that a classic peptidic coupling reaction could occur between two pseudopeptidic units. The continuation of the study was made on solid phase and allowed us to obtain the first [alpha-N-amino]peptides never synthesized to this day. Finally, in the third chapter, these oligomers were studied by molecular modelling and various spectroscopic methods (NMR, IR) who allowed to suggest a folding by the establishment of intramolecular hydrogen bonds
Fairfull-Smith, Kathryn Elizabeth, and n/a. "Synthetic and Mechanistic Investigations of Some Novel Organophosphorus Reagents." Griffith University. School of Science, 2004. http://www4.gu.edu.au:8080/adt-root/public/adt-QGU20040917.081950.
Full textFairfull-Smith, Kathryn Elizabeth. "Synthetic and Mechanistic Investigations of Some Novel Organophosphorus Reagents." Thesis, Griffith University, 2004. http://hdl.handle.net/10072/367534.
Full textThesis (PhD Doctorate)
Doctor of Philosophy (PhD)
School of Science
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Woods, Timothy E. "Elucidating the degree of selectivity for NLO surrogate attachment to model compounds and a co-polyimide using the Mitsunobu reaction /." Online version of thesis, 2008. http://hdl.handle.net/1850/7725.
Full textAzzouz, Rabah. "Pyridinols protégés et leur utilisation en métallation. Synthèse d'indolizidines à partir de la pyridine : synthèse d'indolizidines à partir de la pyridine." Phd thesis, INSA de Rouen, 2008. http://tel.archives-ouvertes.fr/tel-00559656.
Full textFang, Fang. "Synthesis of Bicyclic and Tricyclic Analogues of Oxazolidinone." Ohio University / OhioLINK, 2013. http://rave.ohiolink.edu/etdc/view?acc_num=ohiou1357312054.
Full textAzzouz, Rabah. "Pyridinols protégés et leur utilisation en métallation. Synthèse d'indolizidines à partir de la pyridine : synthèse d'indolizidines à partir de la pyridine." Electronic Thesis or Diss., Rouen, INSA, 2008. http://www.theses.fr/2008ISAM0004.
Full textWe report that the tetrahydropyranylation of pyridinols and phenols, exhibiting especially very low nucleophilicities, can be achieved by means of Mitsunobu reaction with 2-hydroxy-tetrahydropyran. We studied the regioselective deprotonation of 3- an 4-(tetrahdropyran-2-yloxy)pyridines with n-butyllithium. Trapping the lithiated species with various electrophiles afforded functionalized pyridines in good yields. A one-pot procedure also allowed the double fuctionalization at C4 and C2 in the case of 3-O-THP-pyridine. The ortho-metallating ability of this group was examined in comparison with other well-known oxygen-based ortho-directing groups. A four-step synthesis of (-)-lentiginosine and its epimers is described starting from 2-bromopyridine. The key step consisted of a quaternarization of a fully unprotected pyridinium-polyol unit using Mitsunobu methodology. We have demonstrated that the Mitsunobu reaction is viable as a new methodology for the N-alkylation of pyridine and for the formation of bridgehead azabicyclic compounds from pyridine derivatives
Hémelaere, Rémy. "Mise au point de réactions tandems catalytiques incluant une étape d'isomérisation pour la synthèse de molécules naturelles." Thesis, Rennes 1, 2013. http://www.theses.fr/2013REN1S173/document.
Full textSome of the new challenges of modern synthetic chemistry are: atom economy, employment of catalytic processes, avoidance of toxic reactants and limitation of purification steps. A lot of work has been devoted to the development of tandem reactions. A new reactivity could be generated in a molecule thanks to an isomerisation (or migration) reaction of an alkene. This reaction often needs an hydride specie which comes from a transition metal catalyst. This PhD thesis is about the development of new tandem reactions in which at least one step is an isomerisation of an olefin. A great attention has been dedicated to the synthesis of vinylboronates especially with a cross-metathesis strategy. These intermediates are of great importance in organic chemistry and can be useful in a wide range of reactions. One of those reactions is the transformation of vinylboronates to allylboronates thanks to an isomerisation step. Allylboronates can then react with aldehydes to generate homoallylic alcohols with total diastereoselectivity. These new reactions have found applications in total synthesis of natural molecules with a 2,3-dihydrobenzofuran core
Garzon, Cecile. "Développement de réactions organocatalysées et de métathèse cyclisante pour la synthèse de vinylphosphonates hétérocycliques et carbocycliques à potentialités biologiques." Thesis, Aix-Marseille 3, 2011. http://www.theses.fr/2011AIX30034.
Full textFunctionalized vinylphosphonates constitute an important class of building blocks used in organic synthesis and aroused great interest due to their various biological activities. Thus, we developed several synthetic methodologies to reach these compounds. The most general method entails an organocatalyzed substitution reaction using an original substrate, and allows the synthesis of numerous hitherto unknown vinylphosphonates.Then, the synthesis of azaheterocyclic vinylphosphonates was investigated using the ring closing metathesis from appropriate substrates which are obtained through the above methodology.Finally, we have set up the first enantioselective synthesis of UPF 702 (a cyclic vinylphosphonate including the amino acid moiety), known to exhibit agonist activity towards glutamate receptors, and thus potentially active against central nervous system diseases. Two synthetic approaches were devised, based on the organocatalyzed substitution followed by ring closing metathesis. The enantioselectivity was brought by enzymatic resolution or desymmetrisation, whereas the amino acid was prepared via a Curtius rearrangement
But, Yuen-sze Tracy, and 畢婉詩. "Organocatalytic alcohol oxidation and Mitsunobu reactions." Thesis, The University of Hong Kong (Pokfulam, Hong Kong), 2009. http://hub.hku.hk/bib/B42182578.
Full textBut, Yuen-sze Tracy. "Organocatalytic alcohol oxidation and Mitsunobu reactions." Click to view the E-thesis via HKUTO, 2009. http://sunzi.lib.hku.hk/hkuto/record/B42182578.
Full textGoran, Benedeković. "Enantiodivergentna totalna sinteza odabranih stiril laktona i preliminarno ispitivanje njihove citotoksičnosti." Phd thesis, Univerzitet u Novom Sadu, Prirodno-matematički fakultet u Novom Sadu, 2012. http://dx.doi.org/10.2298/NS20121011BENEDEKOVIC.
Full textEnantiodivergent total syntheses of both (+)- and (−)-enantiomers of goniofufurone, 7-epi-goniofufurone and crassalactone C have been accomplished starting from D-glucose. The key steps of the synthe-sis of 7-epi-(+)-goniofufurone were a stereo-selective addition of phenyl magnesium bromide to a protected dialdose, followed by a stereospecific furano-lactone ring formation by condensation of a partially protected lactole with Meldrum’s acid. The synthesis of (+)-goniofufurone and (+)-crassalactone C required a configurational inversion at C-5 in the common intermediate that was efficiently achieved under the standard Mitsunobu conditions, or alternatively through a sequential oxidation of the benzylic hydroxyl group followed by a stereo-selective reduction with borohydride. A similar approach was applied to the synthesis of the unnatural enantiomers of goniofufurone, 7-epi-goniofufurone and crassalactone C, two novel, conformationally constrained analogues of both (+)- and (−)-goniofufurone (oxetanes 34 and ent-34). as well as the corresponding 7-deoxygenated derivatives (31 and ent-31). We have also developed the first total synthesis of (+)-crassalactone B (2) and an alternative synthesis of (+)-crassalactone C (3) starting from D-glucose. Finally, the synthesized styryl-lactones were evaluated for their antiproliferative activity against a panel of human tumor cell lines.
Garzon, Cecile. "Développement de réactions organocatalysées et de métathèse cyclisante pour la synthèse de vinylphosphonates hétérocycliques et carbocycliques à potentialités biologiques." Electronic Thesis or Diss., Aix-Marseille 3, 2011. http://www.theses.fr/2011AIX30034.
Full textFunctionalized vinylphosphonates constitute an important class of building blocks used in organic synthesis and aroused great interest due to their various biological activities. Thus, we developed several synthetic methodologies to reach these compounds. The most general method entails an organocatalyzed substitution reaction using an original substrate, and allows the synthesis of numerous hitherto unknown vinylphosphonates.Then, the synthesis of azaheterocyclic vinylphosphonates was investigated using the ring closing metathesis from appropriate substrates which are obtained through the above methodology.Finally, we have set up the first enantioselective synthesis of UPF 702 (a cyclic vinylphosphonate including the amino acid moiety), known to exhibit agonist activity towards glutamate receptors, and thus potentially active against central nervous system diseases. Two synthetic approaches were devised, based on the organocatalyzed substitution followed by ring closing metathesis. The enantioselectivity was brought by enzymatic resolution or desymmetrisation, whereas the amino acid was prepared via a Curtius rearrangement
Fu, Yunyi Michael. "Development of a polymer-supported reagent for Trost-Lu isomerization reactions and reagents for Mitsunobu reactions." Click to view the E-thesis via HKUTO, 2008. http://sunzi.lib.hku.hk/hkuto/record/B39793989.
Full textFu, Yunyi Michael, and 付運毅. "Development of a polymer-supported reagent for Trost-Lu isomerization reactions and reagents for Mitsunobu reactions." Thesis, The University of Hong Kong (Pokfulam, Hong Kong), 2008. http://hub.hku.hk/bib/B39793989.
Full textSatpathi, Hirak. "Novel phosphorus containing poly(arylene ethers) as flame retardant additives and as reactant in organic synthesis." Doctoral thesis, Saechsische Landesbibliothek- Staats- und Universitaetsbibliothek Dresden, 2015. http://nbn-resolving.de/urn:nbn:de:bsz:14-qucosa-176136.
Full textLiu, Shi-hao, and 劉士豪. "Stereoselective Glycosylation of exo-galactal by Suzuki-Miyaura reaction and Mitsunobu reaction." Thesis, 2011. http://ndltd.ncl.edu.tw/handle/79414950977383047856.
Full text中國醫藥大學
藥物化學研究所碩士班
99
Herein we report C-arylglycosylation and O-glycosylation of exo-glycals, in which two products are generated in association with Suzuki-Miyaura reaction and Mitsunobu reaction C-arylglycosides were synthesized in moderate to good yields by reaction of exo-glycals and arylboronic acids in the presence of 0.5 equiv. Pd(OAc)2. The C-arylglycosylation reaction of a aryl-Pd complex to exo-glycals double bond followed by syn elimination of HPd(OAc) to provide a carbon-Ferrier type product. Mitsunobu reagent mediated O-glycosylation of exo-glycals have been carried out in moderate yields, in which a mixture of two products are often obtained resulting from Ferrier rearrangement and substraction. The exo-glycals reacte with various phenol derivates to afford glycoside with highly α- Stereosrlective.
Khan, Hina Parveen Afzal. "A Mitsunobu-Michael Reaction Sequence to N-Heterocyclic Variants and Ti(III)-Mediated Synthesis of Terpenoids and N-Fused Indoles." Thesis, 2019. https://etd.iisc.ac.in/handle/2005/4382.
Full textLin, Yu-Li, and 林于莉. "(1)Synthesis of Substituted 5,14-dihydro-8H-13-oxadibenzo[a,f]cyclodecene via Ring-Closing Metathesis(2)Conversion of alcohols into alkyl halides via Mitsunobu reaction." Thesis, 2004. http://ndltd.ncl.edu.tw/handle/94191663620512138344.
Full text高雄醫學大學
醫藥暨應用化學系碩士班
92
Part Ⅰ As part of an ongoing study of the chemistry of benzoheterocyclic compounds, a series of 10-membered macrocyclic ethers annulated with substituted benzene is described. O-allylbenzylalcohols and O-allyl- phenols, derived from isovanillin, were coupled by the Mitsunobu reaction to construct the intramolecular dienes as precursor for ring- closing metathesis (RCM). Finally, by the treatment of Grubbs’ catalyst the intramolecular dienes were cyclized to give the desired compounds, 10-membered macrocyclic ethers, respectively. Part Ⅱ Two new methods for the conversion of alcohols into alkyl chloride are established. Method 1, alcohols were reacted with DIAD, TPP and 2-thiothiazoline to undergo Mitsunobu reaction to produce 2-alkylthio- thiazolines which were subsequently treated with ethyl chloroformate to produce alkyl chlorides in good yields. Mothod 2, alcohols were reacted with triphenylphosphine (TPP), diisopropyl azodicarboxylate (DIAD) in THF, followed by treating with ethyl chloroformate to afford alkyl chlorides in one pot in moderate yields.
Pal, Sunit. "Design, Synthesis and Conformational Analysis of Hydrogen Bond Surrogate (HBS) Stabilized Helices in Natural Sequences. Helically Constrained Peptides for Potential DNA-Binding." Thesis, 2020. https://etd.iisc.ac.in/handle/2005/4837.
Full textCSIR
Geranurimi, Azade. "Lactam-peptide modulators of biased interlukin-1 receptor signaling for mitigating inflammation without compromising immuno-vigilance." Thesis, 2019. http://hdl.handle.net/1866/23926.
Full textPreterm birth (PTB) is an unmet biomedical need. Despite efforts to counter the onset of preterm labor, the rate of premature birth has increased steadily in developed countries. The interleukin-1 receptor (IL-1R) has been pursued as a target for designing agents which can prolong labor and improve neonatal outcomes. Towards these goals, a lead peptide 101.10 had been shown to modulate the IL-1R, to delay PTB and to mitigate associated retinopathy of prematurity (ROP) by an allosteric mechanism featuring biased signaling. With the goals of understanding the active conformers and improving the activity of 101.10, methods were conceived for the synthesis and introduction of β-substituted α-amino γ-lactams into peptides. Applying such methods on 101.10 has provided insight into the structure-activity relationships required for allosteric modulation of the IL-1R. Peptidomimetics are promising structures that replicate peptide function and conformation. They offer the potential to improve molecular-recognition, to enhance transport across biological membranes, and to resist metabolism. Among peptidomimetic classes, α-amino γ-lactam (Agl) residues introduce covalent constraint to rigidify the peptide backbone and have been employed to favor turn secondary structures. β-Substituted Agl analogs offer additional potential to mimic and restrict peptide side-chain geometry. This thesis introduces effective methods for the stereo-controlled synthesis of β-substituted α-amino γ-lactams residues having various side chain functionality. Introduction of the parent Agl residue and β-substituted counterparts into biologically active peptides has been explored to study structure-activity relationships. Employing the IL-1R modulator 101.10 as a representative peptide, the described research has furnished novel labor delaying agents that can improve neonatal outcomes. In chapter 2, α-amino-γ-lactam (Agl) and β-hydroxy-α-amino-γ-lactam (Hgl) stereoisomers were employed to study the influence of configuration and hydroxyl group side chain on conformation and activity of the interleukin-1 receptor modulator peptide 101.10. The configuration and hydroxyl group side chain influenced the conformation and biological activity of Agl and Hgl-101.10 analogs. Circular dichroism (CD) spectroscopy illustrated β-turn conformers for specific analogs, such as [(3R,4S)-Hgl3]-101.10. The Agl and Hgl analogs were examined in a series of in vitro assays and in vivo models of PTB. Contingent on their structure vi and configuration, the lactam analogs exhibited different functional selectivity in the various biological pathways, and indicated the requirement for specific phenotypes. For example, inhibition of the JNK and ROCK kinase pathways were respectively shown to be important for delaying labor and diminishing vaso-obliteration in the PTB and ROP models. Notably, among the twelve analogs, [(3R,4S)-Hgl3]-101.10 was found to exhibit identical in vitro and in vivo activity as the parent peptide. In chapter 3, methods were developed for displacement of the β-hydroxy-α-amino-γ-lactam (Hgl) residue alcohol to introduce stereo-selectively different β-substituents on Agl residues. A combination of Mitsunobu chemistry on the trans Hgl residue, and nucleophilic ring opening of the cyclic sulfamidate derived from the cis lactam counterpart provided constrained mimics of Ser, Thr, Cys, Dap, Dab, His and Met residues. In chapter 4, various β-substituted lactams were introduced into the sequence of 101.10 by combination of solution and solid phases chemistry to further study the structural requirements for regulating the activity and signaling of this key cytokine mediator of inflammasome activation. Considering the activity of [(3R,4S)-Hgl3]-101.10, the β-substituted Agl analogs were synthesized possessing similar backbone and side chain configurations. Certain analogs exhibited promising biological activity in the ROP model meriting further study. In sum, methods were conceived for the synthesis and application of α-amino-γ-lactams and their β-substituted analogs to study peptide structure-activity relationships. Employing this chemistry on the IL-1R allosteric modulator 101.10 has identified the active conformer and in vitro activity responsible for ability to delay labor and mitigate retinopathy of prematurity. Considering the utility of the lactam synthesis methods for the development of improved agents for delaying labor and improving neonatal outcomes, this thesis has conceived useful prototypes for drugs to treat PTB, as well as useful methods for dissecting the structural requirements for peptide chemical biology.