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  • 1.
    Ayesa Alvarez, Susana
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Design and Synthesis of Amine Building Blocks and Protease Inhibitors2008Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    The first part of this thesis addresses the design and synthesis of amine building blocks accomplished by applying two different synthetic procedures, both of which were developed using solid-phase chemistry. Chapter 1 presents the first of these methods, entailing a practical solid-phase parallel synthesis route to N-monoalkylated aminopiperidines and aminopyrrolidines achieved by selective reductive alkylation of primary and/or secondary amines. Solid-phase NMR spectroscopy was used to monitor the reactions for which a new pulse sequence was developed. The second method, reported in Chapter 2, involves a novel approach to the synthesis of secondary amines starting from reactive alkyl halides and azides. The convenient solid-phase protocol that was devised made use of the Staudinger reaction in order to accomplish highly efficient alkylations of N-alkyl phosphimines or N-aryl phosphimines with reactive alkyl halides.

    The second part of the thesis describes the design and synthesis of three classes of protease inhibitors targeting the cysteine proteases cathepsins S and K, and the serine protease hepatitis C virus (HCV) NS3 protease. Chapter 4 covers the design, solid-phase synthesis, and structure-activity relationships of 4-amidofurane-3-one P1-containing inhibitors of cathepsin S and the effects of P3 sulfonamide groups on the potency and selectivity towards related cathepsin proteases. This work resulted in the discovery of highly potent and selective inhibitors of cathepsin S. Two parallel solid-phase approaches to the synthesis of a series of aminoethylamide inhibitors of cathepsin K are presented in Chapter 5. Finally, Chapter 6 reports peptide-based HCV NS3 protease inhibitors containing a non-electrophilic allylic alcohol moiety as P1 group and also outlines efforts to incorporate this new template into low-molecular-weight drug-like molecules.

  • 2.
    Bielawski, Marcin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Efficient and High-Yielding Routes to Diaryliodonium Salts2008Licentiate thesis, comprehensive summary (Other academic)
    Abstract [en]

    This thesis summarizes three novel and general reaction protocols for the synthesis of diaryliodonium salts. All protocols utilize mCPBA as oxidant and the acids used are either TfOH, to obtain triflate salts, or BF3•Et2O that gives the corresponding tetrafluoroborate salts in situ.

    Chapter two describes the reaction of various arenes and aryl iodides, delivering electron-rich and electron-deficient triflates in moderate to excellent yields.

    In chapter three, it is shown that the need of aryl iodides can be circumvented, as molecular iodine can be used together with arenes in a direct one-pot, three-step synthesis of symmetric diaryliodonium triflates.

    The final and fourth chapter describes the development of a sequential one-pot reaction from aryl iodides and boronic acids, delivering symmetric and unsymmetric, electron-rich and electron-deficient iodonium tetrafluoroborates in moderate to excellent yields. This protocol was developed to overcome mechanistic limitations existing in the protocols described in chapter two and three.

    The methodology described in this thesis is the most general, efficient and high-yielding existing up to date, making diaryliodonium salts easily available for various applications in synthesis.

  • 3.
    Olsson, Ulrika
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Structural Studies of O-antigen polysaccharides, Synthesis of 13C-labelled Oligosaccharides and Conformational Analysis thereof, using NMR Spectroscopy2008Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    In order to understand biological processes, to treat and diagnose diseases, find appropriate vaccines and to prevent the outbreak of epidemics, it is essential to obtain more knowledge about carbohydrate structures. This thesis deals with structure and conformation of carbohydrates, analysed by NMR spectroscopy and MD simulations.In the first two papers, the structures of O-antigen polysaccharides (PS) from two different E. coli bacteria were determined using NMR spectroscopy. The O-antigenic PS from E. coli O152 (paper I) consists of branched pentasaccharide repeating units, built up of three different carbohydrate residues and a phosphodiester, whilst the repeating unit of the O-antigen from E. coli O176 (paper II) is built up of a linear tetrasaccharide consisting of two different monosaccharides.

    In papers III and IV, the conformational analysis of different disaccharides is described. Conformational analysis was performed using NMR spectroscopy and MD simulations (paper IV). In paper III four different glucobiosides were studied using coupling constants and Karplus-type relationships. By use of specific 13C isotopically labelled derivatives, additional coupling constants were obtained and the number of possible torsion angles was reduced by half. In paper IV, we examine the conformations of two disaccharides that are part of an epitope of malignant cells. From NOE and T-ROE experiments, short proton-proton distances around the glycosidic linkage were estimated. Furthermore, interpretation of the extracted coupling constants using Kaplus relationships gave the values of the torsion angles. As in paper III, isotopically labelled compounds were synthesised in order to enhance the sensitivity of the analysis. Finally, MD simulations were performed and the results were compared with results from NMR data.

  • 4.
    Selander, Nicklas
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Development of Multi-Component Reactions using Catalytically Generated Allyl Metal Reagents2008Licentiate thesis, comprehensive summary (Other academic)
    Abstract [en]

    This licentiate thesis is based on the development of catalytic reactions for the synthesis and application of organometallic reagents. By use of palladium pincer-complex catalysts, we have developed an efficient procedure for the synthesis of allylboronates starting from allylic alcohols. These reactions were further extended by including various one-pot multi-component reactions, using the in situ generated allylboronates. Furthermore, novel unsymmetrical palladium pincer-complexes were synthesized and studied in auto-tandem catalysis.

  • 5.
    Zhu, Mingzhao
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Jalalian, Nazli
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    One-pot synthesis of diaryliodonium salts using toluenesulfonic acid - a fast entry to electron-rich diaryliodonium tosylates and triflates2008In: Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, ISSN 0936-5214, E-ISSN 1437-2096, no 4, p. 592-596Article in journal (Refereed)
    Abstract [en]

    A direct synthesis of symmetric and unsymmetric electron-rich diaryliodonium salts is described. The use of MCPBA and toluenesulfonic acid delivers diaryliodonium tosylates in high yields. An in situ anion exchange has also been developed, giving access to the corresponding triflate salts.

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