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  • 1. Alonso, D A
    et al.
    Bertilsson, S K
    Johnsson, S Y
    Nordin, S J M
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry, Organic Chemistry.
    Södergren, M J
    Andersson, Pher G
    New Expidient Route to Both Enantiomers of Nonproteinogenic Amino Acid Derivatives from the Unsaturated 2-Aza-bicyclo Moiety. D. A1999In: J. Org. Chem., Vol. 64, p. 2276-Article in journal (Refereed)
  • 2. Alonso, D A
    et al.
    Nordin, S J M
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry, Organic Chemistry.
    Andersson, Pher G
    Highly Diastereoselective Reaction of 2-Azanorbornyl Enolates with Electrophiles. D. A1999In: Org. Lett., Vol. 1, p. 1595-Article in journal (Refereed)
  • 3. Alonso, D A
    et al.
    Nordin, S J M
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry, Organic Chemistry.
    Roth, P
    Tarnai, T
    Thommen, M
    Pittelkow, U
    Andersson, Pher G
    2-Azanorbornyl alcohols: Very efficient Ligands for Ruthenium-Catalyzed Asymmetric Transfer Hydrogenation of Aromatic Ketones. D. A1999In: J. Org. Chem., Vol. 65, p. 3116-Article in journal (Refereed)
  • 4.
    Alonso, Diego A
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Brandt, P
    Nordin, Sofia J M
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Andersson, Pher G
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Ru(arene)(amino alcohol)-Catalyzed Transfer Hydrogenation of Ketones: Mechanism and Origin of Enantioselectivity1999In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 121, no 41, p. 9580-9588Article in journal (Refereed)
    Abstract [en]

    The mechanism of the Ru(arene)(amino alcohol)-catalyzed transfer hydrogenation of ketones using isopropyl alcohol as the hydrogen source has been studied by means of hybrid density functional methods (B3PW91). Three mechanistic alternatives were evaluated, and it was shown that the reaction takes place via a six-membered transition state, where a metal-bound hydride and a proton of a coordinated amine are transferred simultaneously to the ketone. Further calculations provided a general rationale for the rate of the reaction by comparison of steric effects in the ground and transition states of the ruthenium hydride complex. It was found that the TS has a strong preference for planarity, and this in turn is dependent on the conformational behavior of the O,N-linkage of the amino alcohol ligand. Finally, a general model, rationalizing the enantioselectivity of the reaction, was developed. Experimental studies of both rate and enantioselectivity were used in order to support the computational results.

  • 5.
    Arnaud, Gayet
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry, Organic Chemistry.
    Christelle, Bolea
    Pher G., Andersson
    Development of new camphor based N,S chiral ligands and their application in transfer hydrogenation2004In: Organic & Biomolecular Chemistry, ISSN 1477-0520, Vol. 2, no 13, p. 1887-1893Article in journal (Refereed)
  • 6.
    Arnaud, Gayet
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry, Organic Chemistry.
    Sophie, Bertilsson
    Pher G., Andersson
    Novel Catalytic Kinetic Resolution Of Racemic Epoxides to Allylic alcohols2002In: Organic Letters, ISSN 1523-7060, Vol. 4, no 22, p. 3777-3779Article in journal (Refereed)
  • 7.
    Bergman, Jan
    et al.
    CNT, DEPT ORGAN CHEM, S-14157 HUDDINGE, SWEDEN .
    Lidgren, Göran
    ROYAL INST TECHNOL, DEPT ORGAN CHEM, S-10044 STOCKHOLM 70, SWEDEN.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Synthesis and Reactions of Oxazolones from L‑Tryptophan and α‑Haloacetic Anhydrides1992In: Bulletin des Sociétés chimiques belges, ISSN 0037-9646, Vol. 101, no 7, p. 643-660Article in journal (Refereed)
    Abstract [en]

    Optically active 5(4H)-oxazolones have been synthesized from L-tryptophan and an excess of trifluoro-, trichloro-, and dichloroacetic anhydrides. Some of the 5(4H)-xazolones have been further transformed to the isomeric 5(2H)-oxazolones as well as oxazolones with exocyclic double bonds. Treatment of the various oxazolones under hydrolytic, acidic and Friedel-Crafts acylation conditions gave indole-3-pyruvic acid, alpha,beta-dehydrotryptophans, beta-carbolines as well as the functionalized cyclopentanoindole 32. Treatment of the 4-(3-indolylmethyl)-2-trifluoromethyl-5(2H)-oxazolone (17) with trifluoroacetic acid gave the 3,4-bridged azepinoindole 35.

  • 8.
    Bergström, Sara K.
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Analytical Chemistry.
    Edenwall, Niklas
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Analytical Chemistry.
    Lavén, Martin
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Analytical Chemistry.
    Velikyan, Irina
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Långström, Bengt
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Markides, Karin E.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Analytical Chemistry.
    Polyamine deactivation of integrated poly(dimethylsiloxane) structures investigated by radionuclide imaging and capillary electrophoresis experiments2005In: Analytical Chemistry, ISSN 0003-2700, E-ISSN 1520-6882, Vol. 77, no 3, p. 938-942Article in journal (Refereed)
    Abstract [en]

    The poly(dimethylsiloxane) (PDMS) material provides a number of advantageous features, such as flexibility, elasticity, and transparency, making it useful in integrated analytical systems. Hard fused-silica capillary structures and soft PDMS channels can easily be combined by a tight fit, which offers many alternatives for structure combinations. PDMS and fused silica are in different ways prone to adsorption of low levels of organic compounds. The need for modification of the inner wall surface of PDMS channels may often be necessary, and in this paper, we describe an easy and effective method using the amine-containing polymer PolyE-323 to deactivate both fused-silica and PDMS surfaces. The adsorption of selected peptides to untreated surfaces was compared to PolyE-323-modified surfaces, using both radionuclide imaging and capillary electrophoresis experiments. The polyamine modification displayed a substantially reduced adsorption of three hydrophobic test peptides compared to the native PDMS surface. Filling and storage of aqueous solution were also possible in PolyE-323-modified PDMS channels. In addition, hybrid microstructures of fused silica and PDMS could simultaneously be deactivated in one simple coating procedure.

  • 9. Berlin, Stefan
    et al.
    Ericsson, Cecilia
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry, Organic Chemistry.
    Engman, Lars
    Construction of Tetrahydrofuran-3-ones from Readily Available Organochalcogen Precursors via Radical Carbonylation/Reductive Cyclization2002In: Organic Letters, Vol. 4, p. 3-Article in journal (Refereed)
  • 10. Berlin, Stefan
    et al.
    Ericsson, Cecilia
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry, Organic Chemistry.
    Engman, Lars
    Radical Carbonylation/Reductive Cyclization for the Construction of Tetrahydrofuran-3-ones and Pyrrolidin-3-ones2003In: Journal of Organic Chemistry, Vol. 68, p. 8386-Article in journal (Refereed)
  • 11.
    Beşev, Magnus
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry, Organic Chemistry.
    Radical Cyclization Approaches to Pyrrolidines2002Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    Five-membered rings are readily prepared by 5-exo-trig radical cyclization. This thesis is concerned with novel methodology for pyrrolidine synthesis. We have synthesised selenium containing radical precursors from aziridines and α-phenylseleno ketones, and cyclized them to 2,4- and 3,4-disubstituted pyrrolidines. A few examples of 5-exo-dig cyclization were also demonstrated. In another study we investigated the capacity of the nitrogen protecting group to direct diastereoselectivity in the formation of 2,4-disubstituted pyrrolidines. The diphenylphosphinoyl protecting group directed cyclization to occur in a highly cis-selective manner. When cyclizations were performed at 17 oC, cis/trans-ratios as high as 24/1 were obtained. In contrast, cyclization of the unprotected pyrrolidine precursor afforded the trans-diastereomer as the major product (cis/trans = 1/3.3 – 1/20). We also examined the use of a hydroxyl auxiliary for controlling diastereoselectivity in radical cyclization. The required selenium containing radical precursors were synthesised from 2-cyanoaziridines by addition of organometallic reagents, reduction of the resulting aziridine ketone, and benzeneselenol ring-opening of the aziridine. Cyclization at 17 oC produced 2,4-disubstituted pyrrolidines substantially enriched in the trans-isomer (cis/trans = 1/9 – 1/12). Novel radical cyclization approaches to thiazolines and pyrrolines were also tried.

    The thesis also describes attempts to improve the Hassner aziridine synthesis by employing stannous chloride as a functional group tolerant reducing agent.

  • 12.
    Bäckvall, Jan-Erling
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Andersson, Pher
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Stone, Guy
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Syntheses of (±)-α- and (±)- γ- Lycorane via a Stereocontrolled Organopalladium Route1991In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 56, no 9, p. 2988-2993Article in journal (Refereed)
    Abstract [en]

    Total syntheses of (+/-)-alpha-and (+/-)-gamma-lycorane are described. The key steps in the syntheses are the stereocontrolled palladium-catalyzed intramolecular 1,4-chloroamidation of 12 to 13 and the subsequent anti-stereoselective copper-catalyzed S(N)2' reaction of allylic chloride 13 with [3,4-(methylenedioxy)phenyl]magnesium bromide to give 14. Hexahydroindole 14 has the required relative stereochemistry between carbons 3a, 7, and 7a for alpha-lycorane (1a) and was transformed to the latter via 15 and 16. The epimeric gamma-lycorane (2) was obtained by performing the Bischler-Napieralski cyclization on 14, which led to a highly stereoselective isomerization to give exclusively 17. Compound 17 was subsequently transformed to 2. The overall yield from ester 8 to (+/-)-alpha- and (+/-)-gamma-lycorane was 40 and 36%, respectively.

  • 13. Büttner, Frank
    et al.
    Norgren, Anna S.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry, Organic Chemistry.
    Zhang, Suode
    Prabpai, Samran
    Kongsaeree, Palangpon
    Arvidsson, Per I.
    Cyclic β-tetra- and pentapeptides: Synthesis through on-resin cyclization and conformational studies by X-ray, NMR and CD spectroscopy and theoretical calculations2005In: Chemistry--A European Journal, ISSN 0947-6539, Vol. 11, no 21, p. 6145-6158Article in journal (Refereed)
  • 14.
    Diesen, Jarle Sidney
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Asymmetric Hydrogenations of Imines, Vinyl Fluorides, Enol Phosphinates and Other Alkenes Using N,P-Ligated Iridium Complexes2008Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    The research described in this thesis is directed toward the efficient, enantioselective synthesis of chiral products that have useful functionality. This goal was pursued through catalytic asymmetric hydrogenation, a reaction class that selectively introduces one or two stereocenters into a molecule in an atom-efficient step. This reaction uses a small amount (often <1 mol%) of a chiral catalyst to impart stereoselectivity to the product formed. Though catalytic asymmetric hydrogenation is not a new reaction type, there remain many substrate classes for which it is ineffective. The present thesis describes efforts to extend the reaction to some of these substrates classes. Some of the products synthesized in these studies may eventually find use as building blocks for the production of chiral pharmaceuticals, agrochemicals, or flavouring or colouring agents. However, the primary and immediate aim of this thesis was to develop and demonstrate new catalysts that are rapid and effective in the asymmetric hydrogenation of a broad range of compounds.

    Paper I describes the design and construction of two new, related chiral iridium compounds that are catalysts for asymmetric hydrogenation. They each contain an N,P-donating phosphinooxazoline ligand that is held together by a rigid bicyclic unit. One of these iridium compounds catalyzed the asymmetric hydrogenation of acyclic aryl imines, often with very good enantioselectivities. This is particularly notable because acyclic imines are difficult to reduce with useful enantioselectivity. The second catalyst was useful for the asymmetric hydrogenation of two aryl olefins. In Paper II, the class of catalysts introduced into Paper I is expanded to include many more related compounds, and these are also applied to the asymmetric hydrogenation of prochiral imines and olefins. By studying a range of related catalysts that differ in a single attribute, we were able to probe how different parts of the catalyst affect the yield and selectivity of the hydrogenation reactions.

    Whereas iridium catalysts had been applied to the asymmetric hydrogenation of imines and largely unfunctionalized olefins prior to this work (with varied degrees of success), they had not been used to reduce fluoroolefins. Their hydrogenation, which is discussed in Paper III, was complicated by concomitant defluorination to yield non-halogenated alkanes. To combat this problem, several iridium-based hydrogenation catalysts were applied to the reaction. Two catalysts stood out for their ability to produce chiral fluoroalkanes in good enantioselectivity while minimizing the defluorination reaction, and one of these bore a phosphinooxazoline ligand of the type described in Papers I and II.

    Enol phosphinates are another class of olefins that had not previously been subjected to iridium-catalyzed asymmetric hydrogenation. They do, however, constitute an attractive substrate class, because the product chiral alkyl phosphinates can be transformed into chiral alcohols or chiral phosphines with no erosion of enantiopurity. Iridium complexes of the phosphinooxazoline ligands described in Papers I and II were extremely effective catalysts for the asymmetric hydrogenation of enol phosphinates. They produced alkyl phosphinates from di- and trisubstituted enol phosphinate, β-ketoester-derived enol phosphinates, and even purely alkyl-substituted enol phopshinates, in very high yields and enantioselectivities.

    List of papers
    1. Application of Phosphine-Oxazoline Ligands in Ir-Catalyzed Asymmetric Hydrogenation of Acyclic Aromatic N-Arylimines
    Open this publication in new window or tab >>Application of Phosphine-Oxazoline Ligands in Ir-Catalyzed Asymmetric Hydrogenation of Acyclic Aromatic N-Arylimines
    2004 In: Organic Letters, Vol. 6, no 21, p. 3825-3827Article in journal (Refereed) Published
    Identifiers
    urn:nbn:se:uu:diva-97350 (URN)
    Available from: 2008-05-13 Created: 2008-05-13Bibliographically approved
    2. Hydrogenation of Imines and Olefins Using Phosphine-Oxazoline Iridium Complexes as Catalysts
    Open this publication in new window or tab >>Hydrogenation of Imines and Olefins Using Phosphine-Oxazoline Iridium Complexes as Catalysts
    2006 In: Chemistry-A European Journal, Vol. 12, no 8, p. 2318-2328Article in journal (Refereed) Published
    Identifiers
    urn:nbn:se:uu:diva-97351 (URN)
    Available from: 2008-05-13 Created: 2008-05-13Bibliographically approved
    3. Iridium-Catalyzed Asymmetric Hydrogenation of Fluorinated Olefins Using N,P-Ligands: A struggle with hydrogenolysis and selectivity
    Open this publication in new window or tab >>Iridium-Catalyzed Asymmetric Hydrogenation of Fluorinated Olefins Using N,P-Ligands: A struggle with hydrogenolysis and selectivity
    2007 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 129, no 15, p. 4536-4537Article in journal (Refereed) Published
    Abstract [en]

    To broaden the substrate scope of asymmetric iridium-catalyzed hydrogenation, fluorine-functionalized olefins were synthesized and hydrogenated with iridium complexes. Preliminary results showed high levels of fluorine elimination together with low selectivity. The loss of vinylic fluorine at first seemed difficult to handle, but further studies revealed that a catalyst with an azanorbornyl scaffold in the ligand gave more promising results. With this in mind, a new ligand was developed. This gave among the best results published to date for fluorine asymmetric hydrogenation, yielding high conversion and very high ee's with very little fluorine elimination. Further increasing the selectivity, the trials also revealed that tetrasubstituted fluorine-containing olefins can be hydrogenated with high ee's, despite that this class of compounds has usually shown low reactivity in this reaction type.

    National Category
    Chemical Sciences
    Identifiers
    urn:nbn:se:uu:diva-97352 (URN)10.1021/ja0686763 (DOI)000245739700016 ()17375924 (PubMedID)
    Available from: 2008-05-13 Created: 2008-05-13 Last updated: 2017-12-14Bibliographically approved
    4. Asymmetric Hydrogenation of Di and Trisubstituted Enol Phosphinates with N,P-Ligated Iridium Complexes
    Open this publication in new window or tab >>Asymmetric Hydrogenation of Di and Trisubstituted Enol Phosphinates with N,P-Ligated Iridium Complexes
    2008 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 130, no 16, p. 5595-5599Article in journal (Refereed) Published
    Abstract [en]

    The iridium-catalyzed asymmetric hydrogenation of various di- and trisubstituted enol phosphinates has been studied. Excellent enantioselectivities (up to >99% ee) and full conversion were observed for a range of substrates with both aromatic and aliphatic side chains. Enol phosphinates are structural analogues of enol acetates, and the hydrogenated alkyl phosphinate products can easily be transformed into the corresponding alcohols with conservation of stereochemistry. We have also hydrogenated, in excellent ee, several purely alkyl-substituted enol phosphinates, producing chiral alcohols that are difficult to obtain highly enantioselectively from ketone hydrogenations.

    National Category
    Chemical Sciences
    Identifiers
    urn:nbn:se:uu:diva-97722 (URN)10.1021/ja711372c (DOI)000255041400050 ()
    Available from: 2008-11-11 Created: 2008-11-11 Last updated: 2017-12-14Bibliographically approved
  • 15. El-Sayed, Ibrahim
    et al.
    Guliashvili, Tamaz
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry, Organic Chemistry.
    Hazell, Rita
    Gogoll, Adolf
    Ottosson, Henrik
    Evidence for Formation of Silenes Strongly Influenced by Reversed Si=C Bond Polarity2002In: Organic Letters, ISSN 1523-7060, Vol. 4, no 11, p. 1915-1918Article in journal (Refereed)
  • 16.
    Engman, Lars
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Al-Maharik, Nawaf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    McNaughton, Michael
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Birmingham, A
    Uppsala University.
    Powis, G.
    Uppsala University.
    Thioredoxin Reductase and Cancer Cell Growth Inhibition by Organotellurium Compounds that could be Selectively Incorporated into Tumor Cells2003In: Bioorganic & Medicinal Chemistry, ISSN 0968-0896, E-ISSN 1464-3391, Vol. 11, no 23, p. 5091-5100Article in journal (Refereed)
    Abstract [en]

    The thioredoxins are small ubiquitous redox proteins with the conserved redox catalytic sequence-Trp-Cys-Gly-Pro-Cys-Lys, where the Cys residues undergo reversible NADPH dependent reduction by selenocysteine containing flavoprotein thioredoxin reductases. Thioredoxin expression is increased in several human primary cancers including lung, colon, cervix, liver, pancreatic, colorectal and squamous cell cancer. The thioredoxin/thioredoxin reductase pathway therefore provides an attractive target for cancer drug development. Organotellurium steroid, lipid, amino acid, nucleic base, and polyamine inhibitors were synthesized on the basis that they might be selectively or differentially incorporated into tumor cells. Some of the newly prepared classes of tellurium-based inhibitors (lipid-like compounds 3b and 3e, amino acid derivative 5b, nucleic base derivative 8b, and polyamine derivatives 14a and 14b) inhibited TrxR/Trx and cancer cell growth in culture with IC(50) values in the low micromolar range.

  • 17.
    Engman, Lars
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    McNaughton, Michael
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Gajewska, Malgorzata
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Kumar, Sangit
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Birmingham, Anne
    Powis, Garth
    Thioredoxin reductase and cancer cell growth inhibition by organogold(III) compounds2006In: Anti-Cancer Drugs, ISSN 0959-4973, E-ISSN 1473-5741, Vol. 17, no 5, p. 539-544Article in journal (Refereed)
    Abstract [en]

    Thioredoxin (Trx) expression is increased in several human primary cancers associated with aggressive tumor growth and decreased patient survival, and the Trx/Trx reductase (TrxR) system therefore provides an attractive target for cancer drug development. Various gold(III) compounds with none, one, two or three carbon-gold bonds were evaluated for their capacity to inhibit TrxR and the growth of MCF-7 cancer cells in vitro. Compounds with up to two carbon-gold bonds were often potent inhibitors of TrxR with IC50 values as low as 2 nmol/l. In the presence of Trx and insulin the inhibiting capacity was much lower. However, the inhibitory concentrations of the compounds did not correlate with the ability to kill cells. Out of the organometallics tested, only compound 8 with two carbon-gold bonds was able to inhibit colony formation by MCF-7 breast cancer cells at low micromolar concentrations (IC50=1,6umol/l). Unfortunately, the compound did not show any anti-tumor activity against MCF-7 breast cancer and HT-29 colon cancer zenografts in scid mice.

  • 18.
    Erdélyi, Máté
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry, Organic Chemistry.
    Towards the Development of Photoswitchable β-Hairpin Mimetics2004Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    Peptide secondary structure mimetics are important tools in medicinal chemistry, as they provide analogues of endogeneous peptides with new physicochemical and pharmacological properties. The β-hairpin motif has been shown to be involved in numerous physiological processes, among others in regulation of eucariotic gene transcription. This thesis addresses the design, synthesis and conformational analysis of photoswitchable β-hairpin mimetics.

    The developmental work included the establishment of an improved procedure for cross coupling of aryl halides with terminal alkynes. Microwave mediated Sonogashira couplings in closed vessels were optimized under homogeneous and solid-phase conditions furnishing excellent yields for a large variety of substrates within 5 – 25 minutes. In addition, microwave heating was shown not to have any non-conventional effect on the reaction rate.

    Furthermore, the most important factors affecting β-hairpin stability were evaluated. Studies of tetrapeptide and decapeptide analogues revealed the essential role of the β-turn in initiation of hairpin folding. Moreover, hydrogen bonding was shown to be the main interchain stabilizing force, whereas hydrophobic interactions were found to be relatively weak. Nevertheless, hydrophobic packing appears to provide an important contribution to the thermodynamic stability of β-hairpins.

    Photoswitchable peptidomimetics were prepared by incorporation of various stilbene moieties into tetra- and decapeptides. Synthesis, photochemical isomerisation and spectroscopic conformational analysis of the compounds were performed.

    List of papers
    1. Rapid Homogeneous-Phase Sonogashira Coupling Reactions Using Controlled Microwave Heating
    Open this publication in new window or tab >>Rapid Homogeneous-Phase Sonogashira Coupling Reactions Using Controlled Microwave Heating
    2001 In: Journal of Organic Chemistry, Vol. 66, no 12, p. 4165-4169Article in journal (Refereed) Published
    Identifiers
    urn:nbn:se:uu:diva-91463 (URN)
    Available from: 2004-03-11 Created: 2004-03-11Bibliographically approved
    2. Rapid Microwave Promoted Sonogashira Coupling Reactions on Solid Phase
    Open this publication in new window or tab >>Rapid Microwave Promoted Sonogashira Coupling Reactions on Solid Phase
    2003 (English)In: Journal of Organic Chemistry, Vol. 68, no 16, p. 6431-6434Article in journal (Refereed) Published
    Abstract [en]

    A microwave-enhanced, rapid, and efficient solidphase version of the Sonogashira reaction is presented. It has been applied to the coupling of aryl iodides and bromides with various acetylene derivatives giving excellent yields in 15 to 25 min. The scopes of homogeneous, solventless, and solid-phase conditions for Sonogashira coupling of aryl halides are compared.

    National Category
    Organic Chemistry
    Identifiers
    urn:nbn:se:uu:diva-91464 (URN)10.1021/jo034284s (DOI)
    Available from: 2004-03-11 Created: 2004-03-11 Last updated: 2011-01-05
    3. Insight into β-Hairpin Stability: A Structural and Thermodynamic Study of Diastereomeric β-Hairpin Mimetics
    Open this publication in new window or tab >>Insight into β-Hairpin Stability: A Structural and Thermodynamic Study of Diastereomeric β-Hairpin Mimetics
    2002 In: New Journal of Chemistry, Vol. 26, p. 834-843Article in journal (Refereed) Published
    Identifiers
    urn:nbn:se:uu:diva-91465 (URN)
    Available from: 2004-03-11 Created: 2004-03-11Bibliographically approved
    4. Synthesis and Conformational Analysis of Novel Stibene-type Peptidomimetics
    Open this publication in new window or tab >>Synthesis and Conformational Analysis of Novel Stibene-type Peptidomimetics
    Show others...
    Article in journal (Refereed) Submitted
    Identifiers
    urn:nbn:se:uu:diva-91466 (URN)
    Available from: 2004-03-11 Created: 2004-03-11Bibliographically approved
    5. Synthesis and Conformational Analysis of Novel β-Hairpin mimetics. Factors Affecting Stability and Incorporation of a Photoswitchable Dipeptide Mimic
    Open this publication in new window or tab >>Synthesis and Conformational Analysis of Novel β-Hairpin mimetics. Factors Affecting Stability and Incorporation of a Photoswitchable Dipeptide Mimic
    Article in journal (Refereed) Submitted
    Identifiers
    urn:nbn:se:uu:diva-91467 (URN)
    Available from: 2004-03-11 Created: 2004-03-11Bibliographically approved
  • 19.
    Erdélyi, Máté
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry, Organic Chemistry.
    Gogoll, Adolf
    Rapid Homogeneous-Phase Sonogashira Coupling Reactions Using Controlled Microwave Heating2001In: Journal of Organic Chemistry, Vol. 66, no 12, p. 4165-4169Article in journal (Refereed)
  • 20.
    Erdélyi, Máté
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Gogoll, Adolf
    Rapid Microwave Promoted Sonogashira Coupling Reactions on Solid Phase2003In: Journal of Organic Chemistry, Vol. 68, no 16, p. 6431-6434Article in journal (Refereed)
    Abstract [en]

    A microwave-enhanced, rapid, and efficient solidphase version of the Sonogashira reaction is presented. It has been applied to the coupling of aryl iodides and bromides with various acetylene derivatives giving excellent yields in 15 to 25 min. The scopes of homogeneous, solventless, and solid-phase conditions for Sonogashira coupling of aryl halides are compared.

  • 21.
    Erdélyi, Máté
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry, Organic Chemistry.
    Langer, Vratislav
    Karlén, Anders
    Gogoll, Adolf
    Insight into β-Hairpin Stability: A Structural and Thermodynamic Study of Diastereomeric β-Hairpin Mimetics2002In: New Journal of Chemistry, Vol. 26, p. 834-843Article in journal (Refereed)
  • 22.
    Erdélyi, Máté
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry, Organic Chemistry.
    Nurbo, Johanna
    Niklason, Ida
    Karlén, Anders
    Gogoll, Adolf
    Synthesis and Conformational Analysis of Novel Stibene-type PeptidomimeticsArticle in journal (Refereed)
  • 23.
    Erdélyi, Máté
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry, Organic Chemistry.
    Persson, Åsa
    Karlén, Anders
    Gogoll, Adolf
    Synthesis and Conformational Analysis of Novel β-Hairpin mimetics. Factors Affecting Stability and Incorporation of a Photoswitchable Dipeptide MimicArticle in journal (Refereed)
  • 24.
    Ericsson, Cecilia
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry, Organic Chemistry.
    Synthesis of Tetrahydrofuran and Pyrrolidine Derivatives Utilising Radical Reactions: Organochalcogenides in Reductive, Carbonylative and Group-Transfer Cyclisation2004Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    This thesis describes free-radical reactions for the construction of tetrahydrofuran and pyrrolidine derivatives. The studies are concerned with (i) diastereoselectivity in radical cyclisation, (ii) construction of tetrahydrofuran-3-ones and pyrrolidin-3-ones via radical carbonylation/cyclisation and (iii) synthesis of tetrahydrofuran derivatives via group-transfer cyclisation of organochalcogen compounds.

    (i) Diastereoselectivity in the synthesis of tetrahydrofuran derivatives via radical cyclisation was controlled by addition of Lewis acids. In the synthesis of 2,4-disubstitued tetrahydrofurans, the trans-isomer was formed as the major product in the unperturbed reaction. Upon addition of trialkylalumiums the diastereoselectivity was reversed. In a similar fashion, exo/endo-diastereoselectivity in the synthesis of bicyclic 2,3,4-trisubstituted tetrahydrofurans could also be controlled.

    (ii) Procedures for construction of tetrahydrofuran-3-ones and pyrrolidin-3-ones were presented. Epoxides were ring-opened with benzeneselenolate or benzenetellurolate and the resulting β-hydroxyalkyl phenyl chalcogenides were vinylated using ethyl propiolate/NMM or E-1,2-bis(phenylsulfonyl)ethylene/NaH. The corresponding nitrogen analogues were accessed by N-vinylation of aziridines followed by benzeneselenolate ring-opening. The two types of organochalcogen radical precursors were then treated with TTMSS/AIBN under an atmosphere of carbon monoxide (80 atm) to afford tetrahydrofuran-3-ones and pyrrolidin-3-ones, respectively, in high yields.

    (iii) Microwaves were found to induce group-transfer cyclisation of β-allyloxyalkyl aryl chalcogenides. Short time heating (3-10 min) at 250 oC in ethylene glycol was required to obtain tetrahydrofuran derivatives in 60-91% yield.

    List of papers
    1. Diastereocontrol by Trialkylaluminums in the Synthesis of Tetrahydrofurans via Radical Cyclisation
    Open this publication in new window or tab >>Diastereocontrol by Trialkylaluminums in the Synthesis of Tetrahydrofurans via Radical Cyclisation
    2001 In: Organic Letters, Vol. 3, p. 3459-Article in journal (Refereed) Published
    Identifiers
    urn:nbn:se:uu:diva-91437 (URN)
    Available from: 2004-02-26 Created: 2004-02-26Bibliographically approved
    2. Construction of Tetrahydrofuran-3-ones from Readily Available Organochalcogen Precursors via Radical Carbonylation/Reductive Cyclization
    Open this publication in new window or tab >>Construction of Tetrahydrofuran-3-ones from Readily Available Organochalcogen Precursors via Radical Carbonylation/Reductive Cyclization
    2002 In: Organic Letters, Vol. 4, p. 3-Article in journal (Refereed) Published
    Identifiers
    urn:nbn:se:uu:diva-91438 (URN)
    Available from: 2004-02-26 Created: 2004-02-26Bibliographically approved
    3. Radical Carbonylation/Reductive Cyclization for the Construction of Tetrahydrofuran-3-ones and Pyrrolidin-3-ones
    Open this publication in new window or tab >>Radical Carbonylation/Reductive Cyclization for the Construction of Tetrahydrofuran-3-ones and Pyrrolidin-3-ones
    2003 In: Journal of Organic Chemistry, Vol. 68, p. 8386-Article in journal (Refereed) Published
    Identifiers
    urn:nbn:se:uu:diva-91439 (URN)
    Available from: 2004-02-26 Created: 2004-02-26Bibliographically approved
    4. Microwave-Assisted Group-Transfer Cyclisation of Organotellurium Compounds
    Open this publication in new window or tab >>Microwave-Assisted Group-Transfer Cyclisation of Organotellurium Compounds
    Article in journal (Refereed) Submitted
    Identifiers
    urn:nbn:se:uu:diva-91440 (URN)
    Available from: 2004-02-26 Created: 2004-02-26Bibliographically approved
  • 25.
    Ericsson, Cecilia
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry, Organic Chemistry.
    Engman, Lars
    Diastereocontrol by Trialkylaluminums in the Synthesis of Tetrahydrofurans via Radical Cyclisation2001In: Organic Letters, Vol. 3, p. 3459-Article in journal (Refereed)
  • 26.
    Ericsson, Cecilia
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry, Organic Chemistry.
    Engman, Lars
    Microwave-Assisted Group-Transfer Cyclisation of Organotellurium CompoundsArticle in journal (Refereed)
  • 27.
    Eriksson, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Synthesis of 11C-labelled Alkyl Iodides: Using Non-thermal Plasma and Palladium-mediated Carbonylation Methods2006Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    Compounds labelled with 11C (β+, t1/2 = 20.4 min) are used in positron emission tomography (PET), which is a quantitative non-invasive molecular imaging technique. It utilizes computerized reconstruction methods to produce time-resolved images of the radioactivity distribution in living subjects.

    The feasibility of preparing [11C]methyl iodide from [11C]methane and iodine via a single pass through a non-thermal plasma reactor was explored. [11C]Methyl iodide with a specific radioactivity of 412 ± 32 GBq/µmol was obtained in 13 ± 3% decay-corrected radiochemical yield within 6 min via catalytic hydrogenation of [11C]carbon dioxide (24 GBq) and subsequent iodination, induced by electron impact.

    Labelled ethyl-, propyl- and butyl iodide was synthesized, within 15 min, via palladium-mediated carbonylation using [11C]carbon monoxide. The carbonylation products, labelled carboxylic acids, esters and aldehydes, were reduced to their corresponding alcohols and converted to alkyl iodides. [1-11C]Ethyl iodide was obtained via palladium-mediated carbonylation of methyl iodide with a decay-corrected radiochemical yield of 55 ± 5%. [1-11C]Propyl iodide and [1-11C]butyl iodide were synthesized via the hydroformylation of ethene and propene with decay-corrected radiochemical yields of 58 ± 4% and 34 ± 2%, respectively. [1-11C]Ethyl iodide was obtained with a specific radioactivity of 84 GBq/mmol from 10 GBq of [11C]carbon monoxide. [1-11C]Propyl iodide was synthesized with a specific radioactivity of 270 GBq/mmol from 12 GBq and [1-11C]butyl iodide with 146 GBq/mmol from 8 GBq.

    Palladium-mediated hydroxycarbonylation of acetylene was used in the synthesis of [1-11C]acrylic acid. The labelled carboxylic acid was converted to its acid chloride and subsequently treated with amine to yield N-[carbonyl-11C]benzylacrylamide. In an alternative method, [carbonyl-11C]acrylamides were synthesized in decay-corrected radiochemical yields up to 81% via palladium-mediated carbonylative cross-coupling of vinyl halides and amines. Starting from 10 ± 0.5 GBq of [11C]carbon monoxide, N-[carbonyl-11C]benzylacrylamide was obtained in 4 min with a specific radioactivity of 330 ± 4 GBq/µmol.