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  • 1. Jonsson, Sandra Y.
    Selective functionalisation of carbon-carbon double bonds: dihydroxylation of olefins by H₂O₂ & transformation of sulfonyl 1,3-dienes2002Doctoral thesis, comprehensive summary (Other academic)
  • 2.
    Jönsson, Daniel
    Stockholm University, Faculty of Science, Department of Neurochemistry and Neurotoxicology.
    Applications of multi-component condensations and development of polyamine synthesis on solid-phase2002Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    Solid-phase synthesis of small non-polymeric molecules has become increasingly important as a tool in the development of pharmacologically active compounds. Of particular interest are the syntheses of compounds with low molecular weight, low polarity and a reduced flexibility of the functional groups, i.e. physiochemical properties typical for the majority of drugs currently in use.

    The first part of this thesis describes the synthesis of polycyclic structures with constrained conformation, by the application of multi-component condensations on solid-phase. The 8-azabicyclo[3.2.1]octan-3-one structure of the tropane alkaloids was synthesized on solid-phase by a modification of the well known Robinson tropinone synthesis. The 3-component reaction was performed with the amino component anchored to a solid support, consisting of polyethyleneglycol-grafted polystyrene. Treatment of the primary amine with 1,3-acetonedicarboxylic acid and excess of succinaldehyde, resulted in high purity of the corresponding tropane derivative. Further derivatization of the resin-bound tropane derivative was performed by reduction of the keto-group and acylation of the hydroxyl-group.

    The oxygen-bridged tetrahydropyridones are relatively complex polycyclic structures, which previously have been synthesized in solution by condensation of primary amines, coumarin-3-carboxylic acid and ketones. In the evaluation of a solid-phase approach of this 3-component condensation, several members of this class of compounds were synthesized with the amine anchored to a solid support. The yield and purity of the products were dependent on the ketones used in the reaction, but the expected products were obtained using both acyclic and cyclic ketones and substituted acetophenones.

    The second part of this thesis describes the development of a solid-phase polyamine synthesis. The polyamines are a class of compounds with a wide range of pharmacological and physiological effects, which are constituents in many types of venoms of wasps and spiders. Synthesis of polyamines in homogenous solution is accompanied with several problems concerning selectivity, work-up and yield. By employing a solid-phase approach, a rapid and convenient method for synthesis of polyamines is achieved. In the developed protocol, acid labile benzhydryls are used as amino-protecting groups. The polyamine backbone is assembled sequentially by reductive alkylation of the protected secondary amine with Fmoc-amino aldehydes. The protecting groups allow the use of excess of aldehyde, to avoid underivatized amines, without the risking dialkaylation of the amines, which occurs during reductive alkylations of primary amines with unhindered aliphatic aldehydes. The versatility of the method is displayed by a convenient synthesis of four analogues of a wasp toxin, philanthotoxin.

  • 3.
    Kjellgren, Johan
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabó, Kálmán J.
    Synthesis of stereodefined vinyl-tetrahydropyran and vinyl-octahydrochromene derivatives via acetalization-cyclization of allylsilanes with aldehydes: Origin of the high stereoselectivity2002In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 43, no 6, p. 1123-1126Article in journal (Refereed)
  • 4.
    Larsson, Andreas
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ulicny, Jozef
    Laaksonen, Aatto
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Analysis of NMR J couplings in partially protected galactopyranosides*2002In: Organic Letters, ISSN 1523-7052, Vol. 4, no 11, p. 1831-1834Article in journal (Refereed)
    Abstract [en]

    Hydrogen bond mediated NMR J couplings offer additional structural information. The interpretation of these usually small hJ couplings are,however, not necessarily straightforward. In the present case of a carbohydrate system, a four-bond classical W coupling, 4JHO4,H5, is morereasonable on the basis of, in particular, density functional theory calculations of spin-spin coupling constants at the UB3LYP/6-311G** levelof theory.

  • 5.
    Löfstedt, Joakim
    Stockholm University.
    Selective palladium-catalyzed 1,4-functionalization: allenes and dienes in palladium chemistry and total syntheses of (+)-pseudoconhydrine and (+)-monomorine I2002Doctoral thesis, comprehensive summary (Other academic)
  • 6.
    Nilsson, Johan
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Stawinski, Jacek
    Oxidative Coupling of H-Phosphonate and H-Phosphonothioate Diesters: Iodine as a Reagent and a Catalyst2002In: Collection Symposium Series, Vol. 5, p. 87-92Article in journal (Refereed)
  • 7.
    Olofsson, Berit
    et al.
    Royal Institute of Technology, Sweden.
    Somfai, Peter
    Royal Institute of Technology, Sweden.
    A regio- and stereodivergent route to all isomers of vic-amino alcohols2002In: Latvijas Journal of Chemistry, ISSN 0868-8249, Vol. 1, p. 69-78Article in journal (Refereed)
  • 8.
    Olofsson, Berit
    et al.
    Royal Institute of Technology, Sweden.
    Somfai, Peter
    Royal Institute of Technology, Sweden.
    A regio- and stereodivergent route to all isomers of vic-amino alcohols2002In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 67, no 24, p. 8574-8583Article in journal (Refereed)
    Abstract [en]

    Vicinal amino alcohols are substructures in several important natural products. They are also frequently employed ligands in asymmetric synthesis. Many enantioselective syntheses of vic-amino alcohols have been reported, but each structure has required its own synthetic route. This study presents a synthetic strategy leading to all eight possible isomers of a given beta-amino alcohol, starting from vinyl epoxides. The developed strategy focuses on the propensity of vinyl epoxides and vinylaziridines to be selectively ring-opened at the allylic position by suitable hard nucleophiles. Within this strategy, a novel large-scale aminolysis reaction and the synthesis of a trisubstituted N-H vinylaziridine are detailed.

  • 9.
    Olofsson, Berit
    et al.
    Royal Institute of Technology, Sweden.
    Wijtmans, Roel
    Royal Institute of Technology, Sweden.
    Somfai, Peter.
    Royal Institute of Technology, Sweden.
    Synthesis of N-H vinylaziridines: a comparative study2002In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 58, no 30, p. 5979-5982Article in journal (Refereed)
    Abstract [en]

    Vinylaziridines are useful and versatile synthetic intermediates, as the relief of ring-strain provides a driving force for efficient ring-opening or ring-expansion reactions. Furthermore, the vinyl group can be derivatized into interesting functionalities. The ring-closure of vicinal amino alcs. constitutes a straightforward route to aziridines. Several methods exist for this transformation, although many cannot be applied to vinylaziridines due to their acid lability. This comparative study describes the most effective sequences for the formation of N-H vinylaziridines.

  • 10.
    Oscarsson, Karin
    Stockholm University.
    Rational design and synthesis of protease inhibitors: targeting HIV-1, Malaria Plm I and II and Hepatitis C virus NS3 proteases2002Doctoral thesis, comprehensive summary (Other academic)
  • 11.
    Sehgelmeble, Fernando W.
    Stockholm University.
    Stereospecific synthesis of β-D-fructofuranosides: synthesis of sucrose and structures related to plant and bacterial polysaccharides2002Doctoral thesis, comprehensive summary (Other academic)
  • 12.
    Sigurdsson, Susannah
    Stockholm University.
    Studies aimed at improving the H-phosphonate approach for solid phase oligonucleotide synthesis2002Doctoral thesis, comprehensive summary (Other academic)
  • 13.
    Winqvist, Anna
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Studies towards a method for incorporation of 3'-deoxy-3'-C-methylenephosphonate linkages into oligonucleotides2002Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    Synthetic strategies towards 3’-deoxy-3’-C-methylenephosphinate building blocks were explored. The key transformations involved stereoselective hydroboration of 1-[2-O-(tert-butyldimethylsilyl-5-O-(4-methoxytrityl)-3-deoxy-3-C-methylene- ß -D-erythro-pentofuranosyl]uracil to give the corresponding 3’-deoxy-3’-C- hydroxymethyl derivative with ribo-configuration, as well as the further conversion into a precursor with a suitable leaving group, e. g., triflate, for subsequent substitution with the phosphinic acid synthon bis(trimethylsilyl)hypophosphite. Improvements of these steps enabled synthesis of 2’-O-(tert-butyldimethylsilyl-5’-O-( 4-methoxytrityl)-3’-deoxy-3’-C-methylenephosphinate uridine in a respectable overall yield of 40% over 6 steps, from the corresponding 2’-O-(tert-butyldimethylsilyl- 5’-O-(4-methoxytrityl)uridine.

    For the introduction of internucleosidic 3’-deoxy-3’-C-methylenephosphonate linkages into oligonucleotides, a preparatory study of the elongation steps, i. e., coupling of the phosphinate building block to the 5’-hydroxyl function of a nucleoside derivative and subsequent oxidation, was performed. Of several coupling reagents studied for the activation of the phosphinate building block prior to coupling, the most promising proved to be N,N-bis(2-oxo-3-oxazolidin-1-yl)phosphinic chloride. The oxidation of the resulting 3’-deoxy-3’-C-methylenephosphinate ester to the corresponding 3’-deoxy-3’-C-methylenephosphonate linkage was achieved using iodine in pyridine-water, in the presence of a catalyst, i. e., either a base (triethylamine) or an acid (pyridinium salt).

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