uu.seUppsala University Publications
Change search
Refine search result
1 - 26 of 26
CiteExportLink to result list
Permanent link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
Rows per page
  • 5
  • 10
  • 20
  • 50
  • 100
  • 250
Sort
  • Standard (Relevance)
  • Author A-Ö
  • Author Ö-A
  • Title A-Ö
  • Title Ö-A
  • Publication type A-Ö
  • Publication type Ö-A
  • Issued (Oldest first)
  • Issued (Newest first)
  • Created (Oldest first)
  • Created (Newest first)
  • Last updated (Oldest first)
  • Last updated (Newest first)
  • Disputation date (earliest first)
  • Disputation date (latest first)
  • Standard (Relevance)
  • Author A-Ö
  • Author Ö-A
  • Title A-Ö
  • Title Ö-A
  • Publication type A-Ö
  • Publication type Ö-A
  • Issued (Oldest first)
  • Issued (Newest first)
  • Created (Oldest first)
  • Created (Newest first)
  • Last updated (Oldest first)
  • Last updated (Newest first)
  • Disputation date (earliest first)
  • Disputation date (latest first)
Select
The maximal number of hits you can export is 250. When you want to export more records please use the Create feeds function.
  • 1.
    Arvela, Riina K
    et al.
    University of Connecticut, Department of Chemistry.
    Leadbeater, Nicholas E
    University of Connecticut, Department of Chemistry.
    Collins, Michael J
    CEM Microwave Technology.
    Automated batch scale-up of microwave-promoted Suzuki and Heck coupling reactions in water using ultra-low catalyst concentrations2005In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 61, no 39, p. 9349-9355Article in journal (Refereed)
    Abstract [en]

    Representative Suzuki and Heck couplings in water using ultra-low catalyst concentrations have been scaled-up using an automated batch stop-flow microwave apparatus. Our scale-up methodology shows proof of concept and is easy, fast and cheap to run.

  • 2.
    Ax, Anna
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Joshi, Advait A.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Orrling, Kristina M.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Vrang, Lotta
    Samuelsson, Bertil
    Hallberg, Anders
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Karlén, Anders
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Larhed, Mats
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Synthesis of a small library of non-symmetric cyclic sulfamide HIV-1 protease inhibitors2010In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 66, no 23, p. 4049-4056Article in journal (Refereed)
    Abstract [en]

    A set of 11 non-symmetric cyclic sulfamide HIV-1 protease inhibitors were synthesized and evaluated. The use of a key microwave-assisted silver(I) oxide mediated selective mono N-benzylation reaction enabled fast and straightforward synthesis. The K-i values of the new inhibitors ranged between 0.28 mu M and >20 mu M.

  • 3.
    Bergman, Jan
    et al.
    Department of Organic Chemistry, CNT, Novum Research Park, S-141 52 Huddinge Sweden.
    Venemalm, Lennart
    Department of Organic Chemistry, Royal Institute of Technology, 8-100 44 Stockholm Sweden.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Synthesis of cyclopent[b]indolones1990In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 46, no 17, p. 6067-6084Article in journal (Refereed)
    Abstract [en]

    A number of cyclopent[b]indol-1-ones as well as -3-ones have been synthesized, using a new methodology involving intramolecular ring closure of α,β-unsaturated acylindoles. In some cases 1,2,3,4-tetrahydrocarbazol-4-ones were obtained. This methodology was used in the syntheses of the indole alkaloid yuehchukene and the carbazole alkaloid analogue demethoxycarbazomycin B.

  • 4. Claerhout, Stijn
    et al.
    Sharma, Sweta
    Sköld, Christian
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Cavaluzzo, Claudia
    Sandström, Anja
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Larhed, Mats
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Thirumal, Meganathan
    Parmar, Virinder S.
    Van der Eycken, Erik V.
    Synthesis of functionalized furopyrazines as restricted dipeptidomimetics2012In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 68, no 14, p. 3019-3029Article in journal (Refereed)
    Abstract [en]

    Herein, an efficient synthetic approach to a furopyrazine scaffold with four points of diversity, starting from 2(1H)-pyrazinones, with dipeptomimetic properties, is presented. R-groups corresponding to amino acid side chains were introduced during the 2(1H)-pyrazinone and subsequent furopyrazine formation. The furopyrazine scaffold was further functionalized with an amino- and a carboxy-terminus resulting in a conformationally restricted dipeptidomimetic scaffold. The carboxy-terminus was introduced via a chemoselective vinylation of the 7-position followed by oxidative cleavage, while the amino-terminus was obtained via Buchwald-Hartwig amidation of the 2-position of the scaffold. The versatility of the synthetic method was demonstrated by the synthesis of a small library of diversely substituted furopyrazines having various amino acid side chains on the four points of diversity. Evaluation with an X-ray structure of the scaffold and computational analysis supports the exploitation of the furopyrazine scaffold as a restricted dipeptide mimic, which can mimic the two central residues of a beta-turn.

  • 5.
    Eklöf, Anders M
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Ottosson, Henrik
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Effects of Substituents and Counterions on the Structures of Silenolates: A Computational Investigation2009In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 65, no 28, p. 5521-5526Article in journal (Refereed)
    Abstract [en]

    The structures and charge distributions of substituted silenolates   [H2SiC(=O)X](-) (X-H, SiH3, Me, t-Bu, OMe, NMe2; group A),  [Y2SiC(=O)H](-) (Y=H, F, Me, Ph, SiH3, SiMe3; group B), and [Y2SiC(=O)X](-) (Y=Me, X=t-Bu, and Y=SiMe3; X=t-Bu, OMe, NMe2; group C)   were examined through density functional theory calculations. The effects of the solvated counterion (K+, Li+, or MgCl+) and coordination site (O or Si) on the properties of group C silenolates were also Studied. The variation in the degree of pi-conjugative reverse SiC bond   polarization, Sigma Phi(RP)(pi) calculated by natural resonance theory,   was determined. The Sigma Phi(RP)(pi) correlated with r(SiC) for both   group A and B silenolates, and the correlation between Sigma   Phi(RP)(pi) and the Sum of valence angles at Si, Sigma alpha(Si), was   good for group A but poor for group B due to strong influence of the   inductive effect. The SiC charge difference correlated well with Sigma   Phi(RP)(pi) for group A, but not for group B, again an effect of   inductive substituent effects. The group C silenolates were Coordinated   to Li(THF)(3)(+), MgCl(THF)(4)(+), and K(THF)(5)(+) either via the O or   Si atom. The coordination energies show that coordination to the hard O   is preferred for Li+ and MgCl+, but the K+ ion coordinated   simultaneously to Si and O. Coordination of the solvated metal ion to O  resulted in shorter SiC bond length, an increased Sigma alpha(Si)   value, and lower Delta q(SiC) when compared to the naked silenolate.  Choice Of counterion and substituent provides a means to extensively vary the properties of silenolates such as their reactivity.

  • 6.
    Garg, Neeraj
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Westerlund, C
    Sundell, S
    Karlen, Anders
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Hallberg, Anders
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Preparation of cis-5-methoxy-and-7-methoxy-1-acetoxy-1,2,3,4,4a,10a-hexahydro-9(10H)-phenanthrenone. An epoxide-arene reaction involving a selective 1,2-alkyl shift rearrangement1996In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 52, no 48, p. 15209-15224Article in journal (Refereed)
    Abstract [en]

    The preparation of cis-1α-acetoxy-7-methoxy-1,2,3,4,4a,10a-hexahydro-9(10H)- phenanthrenone 5 was accomplished starting from 6-methoxy-1-tetralone. Reduction of 7-methoxy-1,2,3, 4,9,10-hexahydro-1-oxo-phenanthrene 8, acetylation and subsequent oxidation delivered 5. Application of an analogus procedure to the preparation of cis-1β-acetoxy-5-methoxy-1,2,3,4,,4a,10a-hexahydro-9(10H)- phenanthrenone 6 was not feasible. A more elaborate route was developed for the synthesis of compound 6, where an epoxide-arene reaction involving a 1,2-alkyl shift rearrangement, constituted a highly selective key transformation.

    The compounds 5 and 6 were prepared. A route was developed for the synthesis of compound 6, where an epoxide-arene reaction involving a 1,2-alkyl shift rearrangement, constituted a highly selective key transformation.

  • 7.
    Gogoll, Adolf
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Oscarsson, Sven
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Biochemistry.
    Reaction of pyridine derivatives with butyl glycidyl ether as a model system for glycidyl ether modified agarose: structural assignment by selective inept spectra1990In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 46, no 7, p. 2539-2548Article in journal (Refereed)
    Abstract [en]

    The reaction of 2-thio-pyridine N-oxide, 2-amino-, 2-hydroxy, 2-thio-, and 4-thiopyridine with butyl glycidyl ether was investigated as a model system for the functionalization of 2,3-epoxypropyl activated agarose. Unambiguous structural assignment of the products was provided by selective INEPT and nuclear Overhauser difference spectra. All reactions were shown to give only one of the possible regioisomers. Further conclusions regarding the structure of the agarose derivatives were drawn from IR spectra.

  • 8. Hao, Yan
    et al.
    Yang, Xichuan
    Cong, Jiayan
    Hagfeldt, Anders
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Physical Chemistry.
    Sun, Licheng
    Engineering of highly efficient tetrahydroquinoline sensitizers for dye-sensitized solar cells2012In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 68, no 2, p. 552-558Article in journal (Refereed)
    Abstract [en]

    Four novel tetrahydroquinoline dyes by inserting isophorone and/or thiophene moieties as pi bridge between the electron donating unit of substituted tetrahydroquinoline and the electron withdrawing unit of cyano carboxylic acid have been synthesized and successfully applied to dye-sensitized solar cells. Among them, DSCs sensitized by HYTIC, which shows the simplest molecular structure, exhibit improved efficiency of 7.0%. This by now is the highest efficiency for the reported tetrahydroquinoline sensitizers and comparable to the performance of N719-sensitized solar cells under the conditions employed here.

  • 9. Johnson, Ann-Louise
    et al.
    Bergman, Jan
    Sjögren, Martin
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Division of Pharmacognosy.
    Bohlin, Lars
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Division of Pharmacognosy.
    Synthesis of barettin2004In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 60, no 4, p. 961-965Article in journal (Refereed)
    Abstract [en]

    The indole alkaloid barettin (with bromine in 6-position), isolated from the marine sponge Geodia Barretti, has been synthesised via a Horner-Wadsworth-Emmons type reaction from 6-bromoindole-3-carboxaldehyde to introduce the dehydro-functionality. Subsequent deprotection and cyclisation afforded the natural product in Z-conformation.

  • 10. Kuhn, Christian
    et al.
    Lindeberg, Gunnar
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Hallberg, Anders
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Schmidt, Boris
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Fmoc protected peptide mimetic based on a cyclohexane framework and incorporation into angiotensin II1997In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 53, no 37, p. 12497-12504Article in journal (Refereed)
    Abstract [en]

    1,3,5-syn substituted cyclohexane based amino acids have been prepared and incorporated into synthetic peptides to serve as scaffold mimicking the Val-Tyr-Ile sequence of angiotensin II. The conformationally constrained tripeptide mimetic holds potential use as a γ-turn replacement.

  • 11.
    Lagerlund, Olof
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Mantel, Mette L. H.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Larhed, Mats
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Aminocarbonylations of Alkenyl Phosphates, Chlorides, Bromides and Triflates with Mo(CO)6 as a Solid CO source2009In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 65, no 36, p. 7646-7652Article in journal (Refereed)
    Abstract [en]

    Palladium-catalyzed aminocarbonylations of alkenyl chlorides, bromides, and triflates were investigated using Mo(CO)6 as a solid carbon monoxide source. The reactions afforded moderate to good yields producing a wide variety of acrylamides after 20 minutes of microwave irradiation. In addition, the aminocarbonylation reaction was, for the first time, expanded to include alkenyl phosphates as starting materials.

  • 12.
    LARHED, M
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    ANDERSSON, CM
    HALLBERG, A
    CHELATION-CONTROLLED, PALLADIUM-CATALYZED ARYLATION OF ENOL ETHERS WITH ARYL TRIFLATES - LIGAND CONTROL OF SELECTION FOR ALPHA-ARYLATION OR BETA-ARYLATION OF [2-(DIMETHYLAMINO)ETHOXY]ETHENE1994In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 50, no 2, p. 285-304Article in journal (Refereed)
    Abstract [en]

    Palladium-catalyzed arylation reactions of [2-(Dimethylamino)ethoxy]ethene (1) with a series of aryl triflates were performed under a variety of reaction conditions. In particular, the influence of phosphine ligands and halide additives on regioselectivity were studied. It was found that the chelation-controlled arylation of 1 affords an expedient route for the conversion of phenols into arylacetaldehydes. Alternatively, the same starting materials could be used to synthesize acetophenones by reversing the regioselectivity with bidentate phosphine ligands.

  • 13. Maldonado, Matias Funes
    et al.
    Sehgelmeble, Fernando
    Bjarnemark, Fanny
    Svensson, Mats
    Ahman, Jens
    Arvidsson, Per I.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Synthesis and arylation of unprotected sulfonimidamides2012In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 68, no 36, p. 7456-7462Article in journal (Refereed)
    Abstract [en]

    Herein we evaluate different methodologies for the synthesis of unprotected sulfonimidamides. Three different procedures that allow orthogonal deprotection of the imine nitrogen under acidic, nucleophilic, and basic conditions were established. Moreover, we present a highly efficient methodology for functionalization of the imine nitrogen through Pd-catalyzed C-N arylation. RuPhos ligand was shown to allow short reaction time, excellent yields, and allowed coupling of both aryl halides and heteroaryl bromides.

  • 14. Maldonado, Matias Funes
    et al.
    Sehgelmeble, Fernando
    Bjarnemark, Fanny
    Svensson, Mats
    Ahman, Jens
    Arvidsson, Per I.
    Synthesis and arylation of unprotected sulfonimidamides2012In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 68, no 36, p. 7456-7462Article in journal (Refereed)
  • 15.
    Mesas-Sanchez, Laura
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Diaz-Alvarez, Alba E.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Koukal, Peter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Diner, Peter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Kinetic resolution of 2-hydroxy-2-aryl-ethylphosphonates by a non-enzymatic acylation catalyst2014In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 70, no 24, p. 3807-3811Article in journal (Refereed)
    Abstract [en]

    Optically pure hydroxyphosphonates are widely used as derivatizable compounds that can be incorporated into a variety of synthetic strategies for the preparation of other high value organic products. A non-enzymatic kinetic resolution procedure to obtain chiral 2-hydroxy-2-arylethylphosphonates from the easily available racemic counterparts is described. A range of 2-hydroxy-2-arylethylphosphonates was efficiently resolved employing a planar-chiral DMAP derived catalyst with good selectivities (up to S=68). The chiral hydroxyphosphonates were isolated in good yields and high enantiomeric excess (>94% ee).

  • 16.
    Mesas-Sánchez, Laura
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Díaz-Álvarez, Alba Estrella
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Dinér, Peter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Non-enzymatic kinetic resolution of 1,2-azidoalcohols using a planar-chiral DMAP derivative catalyst2013In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 69, no 2, p. 753-757Article in journal (Refereed)
    Abstract [en]

    Optically pure 1,2-azidoalcohols are widely used as precursors for other high value organic products. A non-enzymatic kinetic resolution procedure for the stereoselective synthesis of chiral 1,2-azidoalcohols from the readily available racemic counterparts has been developed, employing a planar-chiral DMAP derivative catalyst. Following this procedure, a range of aromatic 1,2-azidoalcohols was obtained in good selectivities (up to S=45) and high enantiomeric excess (up to 99% ee).

  • 17.
    Norrehed, Sara
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Polavarapu, Prasad
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Yang, Wenzhi
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Grennberg, Helena
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Physical Organic Chemistry.
    Conformational restriction of flexible molecules in solution by a semirigid bis-porphyrin molecular tweezer2013In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 69, no 34, p. 7131-7138Article in journal (Refereed)
    Abstract [en]

    A semirigid bis-porphyrin molecular clip with a glycoluril backbone has been synthesized. The clip provides an adaptable molecular cavity for binding of diamines. Binding constants for diamines of 104–107 M−1 are orders of magnitude higher than those for monoamines of 103 M−1, indicating a preference to bidentate binding. NMR studies confirmed that binding of bidentate guests occurs inside the clip. Short- and medium-size acyclic molecular guests are locked into a single, extended conformation, and also guests with longer flexible chains exhibit considerably less conformational mobility than when free in solution. The size of the cavity adapts to the guest size, as indicated by modelling studies and self diffusion constants of the complexes.

  • 18. Nöteberg, Daniel
    et al.
    Brånalt, Jonas
    Kvarnström, Ingemar
    Classon, Björn
    Samuelsson, Bertil
    Nillroth, Ulrika
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry.
    Danielson, Helena
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry.
    Karlén, Anders
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Hallberg, Anders
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry.
    Synthesis of enantiomerically pure cis and trans 2-aminocyclopentanecarboxylic acids. Use of proline replacements in potential HIV-protease inhibitors1997In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 53, no 23, p. 7975-7984Article in journal (Refereed)
    Abstract [en]

    The synthesis of the four diastereomeric 2-aminocyclopentanecarboxylic acids, their use as replacements for proline in potential HIV protease inhibitors containing a hydroxyethylamine dipeptide isostere and the evaluation of the biological activity of these is described.

  • 19.
    Russo, Francesco
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Wångsell, Fredrik
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Sävmarker, Jonas
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Jacobsson, Micael
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Larhed, Mats
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Synthesis and evaluation of a new class of tertiary alcohol based BACE-1 inhibitors2009In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 65, no 48, p. 10047-10059Article in journal (Refereed)
    Abstract [en]

    BACE-1 has emerged as one of the best characterized targets for future   Alzheimer therapy. In accordance with the successful identification of   masked inhibitors of HIV-1 protease, we envisioned that tert-alcohol   containing transition-state mimicking structures would also be   worthwhile evaluating as BACE-1 inhibitors. Twelve novel inhibitors   were prepared via synthetic routes using epoxyalcohol derivates as key   intermediates. The best synthesized tert-hydroxy inhibitor exhibited a   BACE-1 IC50 value of 0.38 mu M.

  • 20.
    Suresh, Surisetti
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Shyamraj, Dharavath
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Larhed, Mats
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Synthesis of antimalarial compounds fosmidomycin and FR900098 through N- or P-alkylation reactions2013In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 69, no 3, p. 1183-1188Article in journal (Refereed)
    Abstract [en]

    Two straightforward and convenient routes for the synthesis of the antimalarial agents FR900098 and fosmidomycin are described. In the key steps N- or P-alkylation reactions are used. The best overall yields of FR900098 and fosmidomycin in 15 mmol scale are 83% and 68%, respectively. These routes utilize readily available materials and avoid harsh conditions.

  • 21.
    Svennebring, Andreas
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Sjöberg, Per
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Physical and Analytical Chemistry, Analytical Chemistry.
    Larhed, Mats
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Nilsson, Peter
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry. ORGFARM.
    A mechanistic study on modern palladium catalyst precursors as new gateways to Pd(0) in cationic Heck reactions2008In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 64, no 8, p. 1808-1812Article in journal (Refereed)
    Abstract [en]

    Electrospray ionization mass spectrometry (ESI-MS) was used as a means to directly identify catalytic cationic organopalladium species in ligand-controlled Heck reactions involving electron-rich olefins and different Pd-sources. In these high-temperature Heck arylations, the oxidative addition intermediates were observed as bidentate ligand chelated cationic aryl palladium species, suggesting that the used ligand attaches to the metal center at the very beginning of the catalytic cycle. This was also in agreement with the obtained regioisomeric profile of the isolated products. The investigation supports the standard Pd(0)/Pd(II) Heck mechanism and provides further insight regarding the conceivable composition of fundamental Pd(II) intermediates in an ongoing Heck reaction.

  • 22.
    Tanner, David
    et al.
    Uppsala University.
    Birgersson, Carin
    Uppsala University.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Luthman, Kristina
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    On the Use of C2-Symmetric Aziridines as Chiral Auxiliaries1994In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 50, no 32, p. 9797-9824Article in journal (Refereed)
  • 23.
    Trejos, Alejandro
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Sävmarker, Jonas
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Schlummer, Stefanie
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Datta, Gopal K.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Nilsson, Peter
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Larhed, Mats
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Stereoselective Heck arylation of a functionalized cyclopentenyl ether using (S)-N-methyl-pyrrolidine as the stereochemical controller2008In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 64, no 37, p. 8746-8751Article in journal (Refereed)
    Abstract [en]

    The study of a series of palladium(0)-catalyzed C2-arylations of a 1-cyclopentenyl ether equipped with a chiral (S)-N-methyl-pyrrolidine auxiliary is reported. Stereoselective Heck monoarylations were performed using aryl iodides under classical heating conditions for 1.7-3.0 h at 80 degrees C and in one case using 30 min of microwave irradiation at 110 degrees C. To further explore the scope and nature of this stereoselective methodology, aryl bromides were also utilized as arylating agents, using 20 min of microwave processing at 120-130 degrees C. High to excellent diastereopurities (90-98% de) were obtained according to H-1 NMR and GC-MS analyses. The prolinol fragment apparently controlled the chastereoselectivity of the Heck reaction by presenting the arylpalladium species from the preferred side of the double bond. By X-ray structure diffraction analysis of an N-quaternized Heck product, the absolute configuration of the new stereocenter was established as (R), Supporting a Si-face migratory insertion.

  • 24.
    Trifonova, Anna
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry, Organic Chemistry.
    Källström, Klas E.
    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.
    Development of a new class of (1S,3R,4R)-2-azabicyclo[2.2.1]heptane-oxazoline ligands and their application in asymmetric transfer hydrogenation2004In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 60, no 15, p. 3393-3403Article in journal (Refereed)
  • 25.
    Wakchaure, Prasad B.
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Bremberg, Ulf
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry. Uppsala University, Science for Life Laboratory, SciLifeLab.
    Wannberg, Johan
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry. Uppsala University, Science for Life Laboratory, SciLifeLab.
    Larhed, Mats
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry. Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Preclinical PET Platform. Uppsala University, Science for Life Laboratory, SciLifeLab.
    Synthesis of enantiopure angiotensin II type 2 receptor [AT(2)R] antagonist EMA4012015In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 71, no 38, p. 6881-6887Article in journal (Refereed)
    Abstract [en]

    We report a facile synthesis of the angiotensin II type 2 receptor antagonist EMA401, which recently passed phase II clinical trials, in high overall yield. The synthesis of the key phenylalanine intermediate involved the formation of an a-nitro cinnamic ester and its reduction followed by a Pictet-Spengler cyclization, which furnished the tetrahydroisoquinoline core structure. Next, EMA401 was separated from its enantiomer EMA402 by four recrystalizations of a diastereomeric salt in 98% ee. All steps were performed on gram scale with emphasis on avoiding column purification and using readily available low cost starting materials and reagents.

  • 26.
    Zhang, Qi
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Norberg, Thomas
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Bergquist, Jonas
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Physical and Analytical Chemistry, Analytical Chemistry.
    Baltzer, Lars
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry II.
    Synthesis of C-11 linked active ester derivatives of vitamin D3 and their conjugations to 42-residue helix–loop–helix peptides2010In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 66, no 25, p. 4577-4586Article in journal (Refereed)
    Abstract [en]

    Derivatives of vitamin D3 carrying an 8-carbon linker at C-11 terminating in an active ester were synthesized from commercial vitamin D3 using a disassembly- ereassembly strategy. Vitamin D3 was cleaved at the C6-C7 double bond and the ‘upper’ fragment was converted, via a series of reactions, to derivatives substituted at C-11 with an 8-carbon linker terminating in an ethyl ester. Reassembly with modified ‘lower’ fragments using Horner-Wittig olefination followed by linker ester hydrolysis and reesterification with p-nitrophenol gave C-11 substituted p-nitrophenyl esters. These vitamin D derivatives were conjugated to 42-amino acid helix-loop-helix peptides by reaction of their p-nitrophenyl esters with lysyl side-chain amino groups on the peptides. The vitamin D-peptide conjugates, being potential specific binder candidates forvitamin D-binding protein, were characterized by mass spectroscopy and CD measurements.

1 - 26 of 26
CiteExportLink to result list
Permanent link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf