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  • 1
    Electronic Resource
    Electronic Resource
    First stereoselective synthesis of (1S,2S,4R,5R)-(-)-β-multistriatin (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 1011-1014 
    Details
    ISSN: 0947-3440
    Keywords: Multistriatin ; 2,3-O-(3-Pentylidene)-D-glyceraldehyde ; Wittig Olefination, cis-selective ; Michael reaction, diastereoselective ; Hydrogenation, diastereoselective ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Starting from 2,3-O-(3-pentylidene)-D-glyceraldehyde (3), we prepared the bicyclic pheromone (1S,2S,4R,5R)-(-)-β-multistriatin (1) on a gram scale. Key steps of the synthesis are a cis-selective Wittig olefination followed by diastereo-selective Michael addition and hydrogenation.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1995199506143
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  • 2
    Electronic Resource
    Electronic Resource
    Zur Problematik der Einteilung von Diels-Alder-Reaktionen in „normale“ und „inverse“Herrn Professor Dr. Rolf Huisgen zu seinem 60. Geburtstag in Verehrung gewidmet. (1981)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1981 (1981), S. 306-311 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: On the Difficulty of Classifying Diels-Alder-Reactions into “Normal” and “Inverse”The reactivity of the investigated cyclic dienophiles with 9,10-dimethylanthracene (7) decreases in the order maleic anhydride (1), maleic thioanhydride (2), and maleic imide (3). An analogous behaviour is equally found for the derivatives 4-6 which are dichlorinated at the double bond. In both series this can be understood with the model of the frontier orbitals only if besides the energies of these orbitals, the differing frontier orbital densities of the dienophiles and the electrophilicity of the diene are also taken into account.
    Notes: Die Reaktivität der untersuchten cyclischen Dienophile gegenüber 9,10-Dimethylanthracen (7) nimmt in der Reihenfolge Maleinsäureanhydrid (1), Maleinsäurethioanhydrid (2) und Maleinsäureimid (3) ab. Ein analoges Verhalten findet man auch für die an der Doppelbindung dichlorierten Derivate 4-6. Innerhalb jeder der beiden Reihen kann dies mit Hilfe des Grenzorbitalmodells nur dann verstanden werden, wenn neben der energetischen Lage der Grenzorbitale auch die unterschiedlichen Grenzorbitaldichten der Dienophile und die Elektrophilie des Diens berücksichtigt werden.
    Additional Material: 5 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198119810214
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  • 3
    Electronic Resource
    Electronic Resource
    Fragmentierung cyclischer Carboxonium-Ionen, IV Synthese von β-Oxa-γ,δ-enonen (1981)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1981 (1981), S. 1105-1117 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Fragmentation of Cyclic Carboxonium Ions, IV.  -  Synthesis of β-Oxa-γ,δ-enonesThe proton-catalyzed fragmentation of 4-methylene-1,3-dioxolanes 2 by weak acids (pK 〉 4.3) or weak acidic ion exchangers leads in good yields to β-oxa-γ,δ-enones 5 which are thus easily and generally available for the first time.
    Notes: Die protonenkatalysierte Fragmentierung der 4-Methylen-1,3-dioxolane 2 mit schwachen Säuren (pK 〉 4.3) oder mit schwach sauren Ionenaustauschern führt in guten Ausbeuten zu den β-Oxa-γ,δ-enonen 5, die damit erstmals einfach und allgemein zugänglich werden.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198119810616
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  • 4
    Electronic Resource
    Electronic Resource
    Carboxonium-Ionen-Reaktionen cyclischer Acetale, VII Synthese von rac-4,5,6,7-Tetrahydro-3,5-dimethyl-1-benzofuran sowie eines Gemisches seiner 3,4- und 3,6-Dimethylisomeren (1982)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1982 (1982), S. 2163-2171 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reactions of Carboxonium Ions of Cyclic Acetals, VII1).  -  Synthesis of rac-4,5,6,7-Tetrahydro-3,5-dimethyl-1-benzofuran and of a Mixture of its 3,4- and 3,6-Dimethyl IsomersThermolysis of the 4-methylene-1,3-dioxolanes 4 or of the β-oxa-γ,δ-enones 6 leads in the presence of protons to rac-4,5,6,7-tetrahydro-3,5-dimethyl-1-benzofuran (5a) and to a mixture of its 3,4- and 3,6-dimethyl isomers 5b/5c. The mechanism of the furan formation has been investigated.
    Notes: Durch Thermolyse der 4-Methylen-1,3-dioxolane 4 oder der β-Oxa-γ,δ-enone 6 entstehen in Gegenwart von Protonen rac-4,5,6,7-Tetrahydro-3,5-dimethyl-1-benzofuran (5a) sowie ein Gemisch von dessen 3,4- und 3,6-Dimethylisomeren 5b/5c. Der Mechanismus der Furanbildung wird untersucht.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198219821207
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  • 5
    Electronic Resource
    Electronic Resource
    Carboxonium-Ionen-Reaktionen cyclischer Acetale, IX. Synthese von Rosenfuran und strukturverwandter terpenoider Ester, Alkohole und Olefine (1986)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1986 (1986), S. 731-740 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reaction of Carboxonium Ions of Cyclic Acetals, IX.  -  Synthesis of Rosefuran and Structurally Related Terpene-like Esters, Alcohols, and OlefinsThermolysis of the 4-(o-toluoyloxy)-1,3-dioxolanes 4 leads to the furans 6/7 which, via Grignard reaction, can be converted into the alcohols 8/9. Subsequent dehydratization affords the olefins 10/11, e.g. rosefuran (10a).
    Notes: Thermolyse der 4-(o-Toluoyloxyl)-1,3-dioxolane 4 führt zu den Furanen 6/7, die via Grignard-Reaktion zu den Alkoholen 8/9 und durch anschließende Dehydratisierung zu den Olefinen 10/11, z. B. Rosenfuran (10a), umgesetzt werden können.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198619860412
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  • 6
    Electronic Resource
    Electronic Resource
    Diastereoselektive Synthese von (1RS)-endo-Brevicomin (1984)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1984 (1984), S. 147-156 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Diastereoselective Synthesis of (1RS)-endo-Brevicomin(1RS-endo-Brevicomin (1) is synthesized starting from trans-1-bromo-2-pentene. Synthetic key step is the diastereoselective linkage of erythro-2,3-butanediol to 3,3-dimethoxy-1-(phenylsulfonyl)-butane or methyl 4,4-dimethoxypentanoate.
    Notes: (1RS)-endo-Brevicomin (1) wird ausgehend von trans-1-Brom-2-penten synthetisiert. Schlüsselreaktion ist die diastereoselektive Verknüpfung von erythro-2,3-Butandiol mit 3,3-Dimethoxy-1-(phenylsulfonyl)butan oder 4,4-Dimethoxypentansäure-methylester.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198419840115
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  • 7
    Electronic Resource
    Electronic Resource
    Darstellung der enantiomeren erythro- und threo-1,2,3-Pentantriole mit Hilfe einer enzymatischen Racematspaltung (1987)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1987 (1987), S. 629-632 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Preparation of Enantiomeric erythro- and threo-1,2,3-Pentanetriols by an Enzymatic Recemate Resolution(2R,3S)- and (2S,3R)-erythro- (9a/9b) as well as (2R,3R)- and (2S,3S)-threo-1,2,3-pentanetriol (10a/10b) are synthesized from the rac. trans- and cis-isomeric 2,3-epoxypentyl butyrates 5/6 by Lipase-controled racemate resolution followed by regioselective ring opening of both the chiral epoxy alcohols 3a/3b and 4a/4b, respectively. Whereas the erythro-triols 9a and 9b are obtained in very good enantiomeric excesses, the reaction sequence yields poor ee values in the case of the threo-triols 10a and 10b.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198719870710
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  • 8
    Electronic Resource
    Electronic Resource
    Synthesis of 3,5-dichloro-6-ethyl-2,4-dihydroxybenzoic acid - the aromatic constituent of lipiarmycin A3 (1991)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1991 (1991), S. 1363-1364 
    Details
    ISSN: 0170-2041
    Keywords: Lipiarmycin ; Macrolide antibiotic ; Benzoic acid, 3,5-dichloro-6-ethyl-2,4-dihydroxy- ; Antibiotics ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 3,5-Dichloro-6-ethyl-2,4-dihydroxybenzoic acid (5, homodichloroorsellinic acid) is the polysubstituted aromatic carboxylic acid found in the macrolide antibiotic lipiarmycin A3. A convenient synthesis of the title compound from ethyl 2-pentenoate and ethyl acetoacetate is described (five steps, 41% overall yield).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1991199101235
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  • 9
    Electronic Resource
    Electronic Resource
    Darstellung von r-1,c-2,t-3,t-4-Cyclobutantetraamin (1979)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1979 (1979), S. 605-607 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of r-1,c-2,t-3,t-4-CyclobutantetraamiePerhydrocyclobuta[1,2-d:3,4-d']diimidazole-2,5-dione (5) has been saponified to r-1,c-2,t-3,t-4-cyclobutanetetraamine tetrahydrobromide (3a, Hal = Br) from which the free amine 3b was obtained. The structure of 3a and 3b was confirmed by 1H-NMR spectroscopy. Some derivatives of 3a and 3b have been prepared.
    Notes: Perhydrocyclobuta[1,2-d:3,4-d']diimidazol-2,5-dion (5) wird zu r-1,c--2,t-3,t-4-cyclobutantetraamin-tetrahybrobromid (3a, Hal = Br) verseift, aus dem das freie Amin 3bgewonnen wird. Die Struktur von 3a und 3b wird 1H-NMR-spektroskopisch bewiesen. Einige Derivate von 3a und 3b werden synthetisiert.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197919790503
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  • 10
    Electronic Resource
    Electronic Resource
    Synthese von (1S)-(-)-Frontalin (1983)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1983 (1983), S. 913-921 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of (1S)-(-)-FrontalinThe aggregation pheromone 1 of the southern pine beetle Dendroctonus frontalis has been synthesized in high optical yield starting from (2R)-2-methyl-2-epoxy-1-propanol (4) which is obtained from methallyl alcohol (3) via enantioselective epoxidation according according to Sharpless9).
    Notes: Das Aggretationspheromon 1 des Borkenkäfers Dendroctonus frontalis wird in hoher optischer Reinheit ausgehend von (2R)-2-Methyl-2-epoxy-1-propanol (4) synthetisiert. 4 wird durch enantioselektive Epoxidierung von Methallylalkohol (3) analog der von Sharpless9) beschriebenen Methode erhalten.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198319830604
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