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  1. Article ; Online: Total Synthesis of (±)-Corymine.

    Zhang, Benxiang / Wang, Xiaoqing / Cheng, Chao / Sun, Deqian / Li, Chaozhong

    Angewandte Chemie (International ed. in English)

    2017  Volume 56, Issue 26, Page(s) 7484–7487

    Abstract: The first total synthesis of the hexacyclic indole alkaloid (±)-corymine is described. Starting from the readily available N-protected tryptamine, the title compound was achieved in 21 steps in 3.4 % overall yield. Key steps of the synthesis include: a) ... ...

    Abstract The first total synthesis of the hexacyclic indole alkaloid (±)-corymine is described. Starting from the readily available N-protected tryptamine, the title compound was achieved in 21 steps in 3.4 % overall yield. Key steps of the synthesis include: a) the addition of a malonate to a 3-bromooxindole to afford 3,3-disubstituted oxindole, b) the formation of a 12-membered cyclic enol ether by intramolecular O-propargylation, immediately followed by propargyl Claisen rearrangement to provide the α-allenyl ketone stereospecifically, c) DMDO oxidation to install a hydroxy group in a highly stereoselective manner, and d) the SmI
    MeSH term(s) Alkaloids/chemical synthesis ; Alkaloids/chemistry ; Indole Alkaloids/chemical synthesis ; Indole Alkaloids/chemistry ; Ketones/chemistry ; Magnetic Resonance Spectroscopy ; Molecular Structure ; Oxidation-Reduction ; Stereoisomerism ; X-Ray Diffraction
    Chemical Substances Alkaloids ; Indole Alkaloids ; Ketones ; corymine (6472-42-0)
    Language English
    Publishing date 2017-05-23
    Publishing country Germany
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.201704086
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article ; Online: Total Synthesis of Notoamides F, I, and R and Sclerotiamide.

    Zhang, Benxiang / Zheng, Weifeng / Wang, Xiaoqing / Sun, Deqian / Li, Chaozhong

    Angewandte Chemie (International ed. in English)

    2016  Volume 55, Issue 35, Page(s) 10435–10438

    Abstract: The total synthesis of the natural indole alkaloids (+)-notoamide F, I, and R and (-)-sclerotiamide is described. The four heptacyclic compounds were synthesized in 10-12 steps in a convergent and highly stereoselective manner from the readily available ... ...

    Abstract The total synthesis of the natural indole alkaloids (+)-notoamide F, I, and R and (-)-sclerotiamide is described. The four heptacyclic compounds were synthesized in 10-12 steps in a convergent and highly stereoselective manner from the readily available Seebach acetal. Key steps of the synthesis include a stereoselective oxidative aza-Prins cyclization to construct the bicyclo[2.2.2]diazaoctane, and a cobalt-catalyzed radical cycloisomerization to create the cyclohexenyl ring.
    Language English
    Publishing date 2016--22
    Publishing country Germany
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.201604754
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article ; Online: Systematic Study of Heteroarene Stacking Using a Congeneric Set of Molecular Glues for Procaspase-6.

    Togo, Takaya / Tram, Linh / Denton, Laura G / ElHilali-Pollard, Xochina / Gu, Jun / Jiang, Jinglei / Liu, Chenglei / Zhao, Yan / Zhao, Yanlong / Zheng, Yinzhe / Zheng, Yunping / Yang, Jingjing / Fan, Panpan / Arkin, Michelle R / Härmä, Harri / Sun, Deqian / Canan, Stacie S / Wheeler, Steven E / Renslo, Adam R

    Journal of medicinal chemistry

    2023  Volume 66, Issue 14, Page(s) 9784–9796

    Abstract: Heteroaromatic stacking interactions are important in drug binding, supramolecular chemistry, and materials science, making protein-ligand model systems of these interactions of considerable interest. Here we studied 30 congeneric ligands that each ... ...

    Abstract Heteroaromatic stacking interactions are important in drug binding, supramolecular chemistry, and materials science, making protein-ligand model systems of these interactions of considerable interest. Here we studied 30 congeneric ligands that each present a distinct heteroarene for stacking between tyrosine residues at the dimer interface of procaspase-6. Complex X-ray crystal structures of 10 analogs showed that stacking geometries were well conserved, while high-accuracy computations showed that heteroarene stacking energy was well correlated with predicted overall ligand binding energies. Empirically determined
    MeSH term(s) Models, Molecular ; Ligands ; Proteins/metabolism ; Tyrosine
    Chemical Substances Ligands ; Proteins ; Tyrosine (42HK56048U)
    Language English
    Publishing date 2023-07-05
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't
    ZDB-ID 218133-2
    ISSN 1520-4804 ; 0022-2623
    ISSN (online) 1520-4804
    ISSN 0022-2623
    DOI 10.1021/acs.jmedchem.3c00590
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

    Zs.B 151: Show issues Location:
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    bis Jg. 2021: Bestellungen von Artikeln über das Online-Bestellformular
    ab Jg. 2022: Lesesaal (EG)
    Zs.MB 1: Show issues

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  4. Article ; Online: Total synthesis of (+)-decursivine.

    Sun, Deqian / Zhao, Qiwu / Li, Chaozhong

    Organic letters

    2011  Volume 13, Issue 19, Page(s) 5302–5305

    Abstract: The first asymmetric synthesis of natural indole alkaloid (+)-decursivine was accomplished. The key step involves the PIFA-mediated intramolecular [3 + 2] cycloaddition of 5-hydroxytryptophan with a substituted cinnamamide in a highly diastereoselective ... ...

    Abstract The first asymmetric synthesis of natural indole alkaloid (+)-decursivine was accomplished. The key step involves the PIFA-mediated intramolecular [3 + 2] cycloaddition of 5-hydroxytryptophan with a substituted cinnamamide in a highly diastereoselective manner.
    MeSH term(s) 5-Hydroxytryptophan/chemistry ; Cinnamates/chemistry ; Cyclization ; Indole Alkaloids/chemical synthesis ; Models, Molecular ; Molecular Structure ; Oxidation-Reduction ; Stereoisomerism
    Chemical Substances Cinnamates ; Indole Alkaloids ; decursivine ; 5-Hydroxytryptophan (C1LJO185Q9) ; cinnamamide (Y0JET56H7N)
    Language English
    Publishing date 2011-10-07
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/ol2021669
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  5. Article ; Online: "Ligand-free" CuI-catalyzed highly efficient intramolecular S-vinylation of thiols with vinyl chlorides and bromides.

    Zhao, Qiwu / Li, Ling / Fang, Yewen / Sun, Deqian / Li, Chaozhong

    The Journal of organic chemistry

    2009  Volume 74, Issue 1, Page(s) 459–462

    Abstract: With CuI as the catalyst and K(3)PO(4) x 3 H(2)O as the base, highly efficient intramolecular S-vinylation of thiols with vinyl chlorides or bromides was successfully implemented without the help of an additional ligand. Moreover, the competition ... ...

    Abstract With CuI as the catalyst and K(3)PO(4) x 3 H(2)O as the base, highly efficient intramolecular S-vinylation of thiols with vinyl chlorides or bromides was successfully implemented without the help of an additional ligand. Moreover, the competition experiments revealed that the 4-exo cyclization is fundamentally preferred over other modes (5-exo, 6-exo, and 6-endo) of cyclization.
    MeSH term(s) Catalysis ; Copper/chemistry ; Iodides/chemistry ; Ligands ; Molecular Structure ; Stereoisomerism ; Sulfhydryl Compounds/chemical synthesis ; Sulfhydryl Compounds/chemistry ; Vinyl Chloride/chemistry ; Vinyl Compounds/chemistry
    Chemical Substances Iodides ; Ligands ; Sulfhydryl Compounds ; Vinyl Compounds ; Copper (789U1901C5) ; cuprous iodide (7DE9CA6IL2) ; vinyl bromide (83NRW59KFY) ; Vinyl Chloride (WD06X94M2D)
    Language English
    Publishing date 2009-01-02
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/jo802235e
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

    Zs.A 4473: Show issues Location:
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