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Showing 1 to 20 of 29 for “"Mitsunobu"”.
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Synthesis of some analogues of n-substituted phthalimide and benzo-tetracyanoquinodimethane
… This thesis will describe the application of the Mitsunobu reaction for the synthesis and identification of N-alkyl derivatives of 3-dicyanomethylene-2,3-dihydroisoindol- 1-one. These derivatives are structural analogues of N-substituted phthalimides and also of benzo-tetracycnoquinodimethane. …
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I. Chemoselective Dehydrative Glycosylation With Application Toward Oligosaccharide Synthesis. II. Sulfide-Mediated Direct Glycosylation of C(1)-Hydroxyl Glycosyl Donors. III. Studies Toward the Total Synthesis of Auriside A
… the Mukaiyama aldol reaction, the intramolecular Mitsunobu macrolactonization, and the Julia olefination for the installation of the C(5)-stereogenic center, the 14-membered macrolactone, and the conjugated bromodiene moiety, respectively.
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Part I: Rapid Synthesis of Dendrimers by an Orthogonal Coupling Strategy. Part II: Design, Synthesis, and Characterization of Hydrogen-Bond Mediated Self-Assembling Dendrimers
… of two AB$\sb2$ building blocks 66 and 67 under Mitsunobu esterification and Sonogashira coupling conditions. Further accelerated growth was achieved by merging the orthogonal coupling strategy with Frechet's branched-monomer approach. Thus, sixth generation dendron 81, with molecular formula …
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Synthesis of nitrogen heterocycles via the intramolecular [4+2] cycloaddition of iminoacetonitriles
… prepared from readily available alcohols via a Mitsunobu reaction with the previously unknown N-cyanomethyltriflamide (HN(Tf)CH₂CN) followed by cesium carbonate promoted elimination of trifluoromethanesulfinate. The a-amino nitrile cycloadducts are versatile synthetic intermediates and can be …
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Synthesis of gemcitabine and it's tetrafluorinated analogues
… methods. In this respect, a high-yielding Mitsunobu-based protocol has also been developed. Both purine and pyrimidine analogues have been synthesised. The aminoglycosylation methodology has been investigated with a range of amines. The methodology proves high-yielding for primary amines …
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Enantiodivergent chemoenzymatic synthesis of codeine
… synthesis of (+)-codeine in 14 steps featuring a Mitsunobu inversion and two intramolecular Heck cyclizations is presented. Investigation of a regioselective nucleophilic opening of a homochiral vinyl oxirane, which led to a total synthesis of the natural isomer of codeine, is detailed. …
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Synthesis of polycyclic heteroaromatic compounds via the intramolecular [4+2] cycloaddition of conjugated hetarenynes and alkynes
… Sonogashira coupling followed in most cases by a Mitsunobu reaction. In the majority of cases metalation of a terminal alkyne with a Grignard reagent and then reaction with various electrophilic reagents allows for the creation of a library of cycloaddition substrates. The scope of the hetarenyne …
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Synthesis of Bicyclic and Tricyclic Analogues of Oxazolidinone
… employing the aziridine-ring-opening and the Mitsunobu reaction, a series of fused bicyclic and tricyclic oxazolidinone-piperazine derivatives have been prepared. Using similar synthetic strategy and subsequent structural modification, the fused tricyclic piperazine analogues of ANB-22/40 have …
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Synthesis of Novel Amino Acids and Peptidomimetics as Tools for Drug Discovery
… The knowledge of Dr. Harris in the field of Mitsunobu alkylation allowed the development of an original strategy for the preparation of racemic amino acids by direct alkylation of an achiral glycine scaffold with stable alcohol electrophiles using modified Mitsunobu reagents. This …
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Fused and spiro furanones from tetronic acid synthons: Oxa and azacycles featuring the butenolide ring
… also formed (five examples were prepared). The Mitsunobu reaction proved to be a better way for the 4-O-alkylation of 3-allyl tetronic acids. 3,3-Diallyldihydrofuran-2,4-diones with two identical allyl residues were obtained by Tsuji-Trost-type Pd-catalysed allylation of either …
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Synthesis Of Natural Product-Based Sphingosine Derivatives
… (±)-30 and (±) -31, via an intramolecular Mitsunobu reaction as a key step. Another crucial technique is the Grubbs' cross-metathesis reaction to the side-chain extension. This reaction provides an opportunity to develop various analogs through side-chain modification. Compound (±)-30 was …
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Design and Synthesis of Novel Benzimidazoles and Aminothiazoles as Small Molecule Inhibitors of CDK5/p25
… C-2 substituted benzimidazoles were achieved via Mitsunobu coupling, Suzuki Miyaura coupling, Buchwald coupling and reductive alkylation strategies. Aminothiazole scaffolds are an established class of CDK inhibitors including CDK5. A molecular hybridization technique was applied to the design of a …
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Synthesis of Resveratrol Esters and Aliphatic Acids.
… diester, 3,5-diacetyloxystilbene <b>(4)</b>. Mitsunobu reaction of 4 and methyl 8-hydroxy-3,6-dioxooctanoate (7) was then carried out to afford methyl 8-(3',5'-diacetyoxystilben-4''-oxy)-3.6-dioxooctanoate <b>(/5)<b>, which was then hydrolyzed to afford <b>9</b> in total 43.6 % yield. …
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Stereoselective monoalkyl diazene synthesis for mild reductive transformations : direct synthesis of densely substituted pyridines and pyrimidines
… intermediates that can be accessed by sequential Mitsunobu displacement, hydrolysis, and fragmentation under mild reaction conditions. II. Stereospecific Palladium-Catalyzed Route to Monoalkyl Diazenes for Mild Allylic Reduction The first single-step stereospecific transition metal-catalyzed …
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Phosphate Tether-Mediated, One-Pot Metathesis Processes: Application in Small Molecule Synthesis
… and diastereoselective cuprate addition and Mitsunobu esterification as key synthetic transformations. Additionally, a phosphorodiamidite coupling and one-pot, sequential RCM/CM/chemoselective hydrogenation sequence was developed to obtain the final molecule in 9 steps from dienediol. The …
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Total Synthesis of Lasionectrin and Synthetic Studies Towards Pestaloxazine A
… unsuccessful. Our revised approach involved Mitsunobu reaction of known alcohol 291 and hydroxamate 311 to give hydroxamic acid 309. However, attempts to effect 1,6-hydrogen abstraction with hydroxamic acid 309 to provide the 1,2-oxazine ring system were unsuccessful.
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Synthesis of phosphorus/sulfur-based antivirals
… of the key carbon-nitrogen bond under Mitsunobu conditions is explored with this strategy ultimately proving unsuccessful. Chapter 4 outlines the preparation of aryl-linked phosphonates and phosphonic acids via copper-catalysed Chan-Lam coupling of adenine-derived nucleobases with …
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Syntheses of novel acyclic amino-amido ligands
… is also detailed. Attempts to this end via the Mitsunobu and Steglich coupling of N,N' -bis[2-(N'',N''- dimethylamino)ethyl]-N'''-(2-hydroxyethyl)iminodiacetamide (100) with N-tertbutyloxycarbonylglycine (105) also met with failure .. Further failed attempts to secure suitably functionalized …
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Stereoselective synthesis of perhydrobenzo[4.5.6]cholestanes
… the corresponding 3α-isomer was obtained through Mitsunobu inversion. Acetoacetylation of the 3-alcohols afforded the corresponding 3β- and 3α-acetoacetoxycholest-4-en-6-ones, which served as substrates for an investigation of intramolecular condensation routes to the target ring systems. Base …
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Total synthesis of naturally occurring glycosylated tetramic acids
… access to aurantosides by employing a Fukayama-Mitsunobu reaction. The behaviour of the tetramic acids, 3-acyl tetramic acids and their boron complexes towards Lewis-acidic glycosylation conditions was examined as well. The last section of this thesis deals with the stereoinduction of the …
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