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  • 1
    Electronic Resource
    Electronic Resource
    Kettenverlängerung von Kohlenhydraten: Synthese von C-Glycosiden und C-Nucleosiden aus Glyconsäuren und Glycarsäuren (1989)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1989 (1989), S. 247-254 
    Details
    ISSN: 0170-2041
    Keywords: Carbohydrates ; Chain elongation ; 1,3-Dicarbonyl compounds ; C-Nucleosides ; Pyrazoles ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Chain Elongation of Carbohydrates: Synthesis of C-Glycosides and C-Nucleosides from Glyconic and Glycaric AcidsBy chain elongation using the C-phenylglycine method allyl residues can be attached to peracetylated glyconic and glycaric acids. Oxidative cleavage of the allylic double bond leads to 1,3-dicarbonyl compounds, which can be converted into optically pure C-glycosides and C-nucleosides by reaction with 1,2-dinucleophiles.
    Notes: Durch Kettenverlängerung mit Hilfe von C-Phenylglycin lassen sich peracetylierte Glyconsäuren und Glycarsäuren mit Allylresten C - C-verknüpfen. Oxidative Spaltung der Allyl-Doppelbindung ergibt 1,3-Dicarbonylverbindungen, aus denen sich durch Ringschlußreaktionen mit 1,2-Dinucleophilen stereochemisch einheitliche C-Glycoside und C-Nucleoside darstellen lassen.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198919890147
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  • 2
    Electronic Resource
    Electronic Resource
    Ester von N-(9-Fluorenylmethyloxycarbonyl)aminosäuren mit 4-Hydroxy-3-oxo-2,5-diphenyl-2,3-dihydrothiophen-1,1-dioxid (Fmoc-Aminosäure-TDO-ester) und ihre Verwendung zur Festphasenpeptidsynthese (1988)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1988 (1988), S. 437-440 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Esters of N-(9-Fluorenylmethoxycarbonyl) Amino Acids with 4-Hydroxy-3-oxo-2,5-diphenyl-2,3-dihydrothiophene 1,1-Dioxide (Fmoc-Amino Acid TDO Esters) and Their Use in Solid Phase Peptide SynthesisFmoc-Amino acid TDO esters 3 are prepared by reaction of Fmoc-amino acids 1 with the cyclic carbonate 2. Their application in peptide synthesis is demonstrated by the preparation of leucylalanylvalylglycine (7) at a p-alkoxybenzyl alcohol resin.
    Notes: Fmoc-Aminosäure-TDO-ester 3 lassen sich durch Umsatz von Fmoc-Aminosäuren 1 mit dem cyclischen Carbonat 2 darstellen. Sie bieten bei Peptidsynthesen Vorteile, die am Beispiel der Darstellung von Leucylalanylvalylglycin (7) an einem p-Alkoxybenzylalkohol-Harz aufgezeigt werden.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198819880511
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  • 3
    Electronic Resource
    Electronic Resource
    Lewis-Säure-katalysierte Umlagerung von 2-Allyl-5(2H)-oxazolonen in Tetrahdro-3H-furo[3,4-b]pyrrol-Derivate (1986)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1986 (1986), S. 1910-1913 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Rearrangement of 2-Allyl-5(2H)-oxazolones into Tetrahydro-3H-furo[3,4-b]pyrrole Derivatives Catalyzed by Lewis AcidsBy Lewis acid catalysis the 2-allyl-5(2H)-oxazolones 1 and 4 rearrange to 6-oxo-3a,4,6,6a-tetrahydro-3H-furo[3,4-b]pyrroles 3 and 5, respectively. The structure of these compounds has been established from their spectroscopic data and by hydrogenation of 5 to the lactone 6. A mechanism for this rearrangement is proposed.
    Notes: Unter Katalyse von Lewis-Säuren lagern sich die 2-Allyl-5(2H)-oxazolone 1 und 4 zu den 6-Oxo-3a,4,6,6,6a-tetrahydro-3H-furo[3,4-b]pyrrolen 3 bzw. 5 um. Die Konstitution dieser Verbindungen wird durch die spektroskopischen Daten und die Hydrogenolyse von 5 zum Lacton 6 bewiesen. Ein Mechanismus für die Umlagerung wird postuliert.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198619861111
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  • 4
    Electronic Resource
    Electronic Resource
    Kettenverlängerung von Kohlenhydraten: Synthese von Pyrazolen aus optisch aktiven Carbonsäuren (1987)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1987 (1987), S. 485-489 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Chain Elongation of Carbohydrates: Synthesis of Pyrazoles from Optically Active Carboxylic AcidsBy chain elongation via the C-phenylglycine method optically active carboxylic acids may be converted into 3-substituted pyrazoles in few steps with good chemical yields. Starting with peracetylated glyconic acids this technique permits an easy access to unprotected C-nucleosides.
    Notes: Durch Kettenverlängerung mit Hilfe von C-Phenylglycin lassen sich optisch aktive Carbonsäuren in wenigen Stufen und guten chemischen Ausbeuten in 3-substituierte Pyrazole überführen. Ausgehend von peracetylierten Glyconsäuren können so auf einfache Weise freie C-Nucleoside dargestellt werden.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198719870361
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  • 5
    Electronic Resource
    Electronic Resource
    Antibiotika aus Basidiomyceten, 28. Hydroxystrobilurin D, ein antifungisches Antibiotikum aus Kulturen von Mycena sanguinolenta (Agaricales) (1988)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1988 (1988), S. 405-409 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Antibiotics from Basidiomycetes, 281). - Hydroxystrobilurin D, an Antifungal Antibiotic from Cultures of Mycena sanguinolenta (Agaricales)The isolation of the antifungal antibiotic hydroxystrobilurin D (3) from cultures of the gilled toadstool Mycena sanguinolenta is described. Its structural elucidation rests on spectroscopic investigations as well as on its thermolytic conversion into the biphenyl derivative 6 which undergoes subsequent acid-catalysed cyclisation to yield the 2H-1,5-benzodioxepine derivative 7. The latter compound proved to be suitable for an assignment of the substituents at the phenyl ring and the determination of the absolute configuration by means of Horeau's method. The biological activities of 3 are discussed.
    Notes: Aus Kulturen des Blätterpilzes Mycena sanguinolenta wird das antifungische Hydroxystrobilurin D (3) isoliert. Seine Strukturaufklärung beruht auf spektroskopischen Untersuchungen sowie auf der Thermolyse zum Biphenylderivat 6, das sich säurekatalysiert in das 2H-1,5-Benzodioxepin-Derivat 7 umwandelt. 7 gestattet die Festlegung der Substituentenanordnung am Benzolring und die Bestimmung der absoluten Konfiguration nach Horeau. Die biologischen Eigenschaften von 3 werden diskutiert.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198819880506
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  • 6
    Electronic Resource
    Electronic Resource
    Oxidation of the fungal sesquiterpene merulidial on alumina gel (1988)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1988 (1988), S. 823-824 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Chromatography of the fungal sesquiterpene merulidial (1a) on alumina gel resulted in its rapid oxidation to give the hydroxylated derivative 2a and the deformylated derivative 3. Compared with compound 4, obtained previously by oxidation of merulidial (1a) with pyridinium chlorochromate, the configuration of the hydroxylated C-9 in compound 2a is inverted.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198819880821
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  • 7
    Electronic Resource
    Electronic Resource
    Kettenverlängerung von Kohlenhydraten mit Hilfe von C-Phenylglycin (1986)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1986 (1986), S. 1548-1567 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Chain Elongation of Carbohydrates via the C-Phenylglycine MethodThe C-phenylglycine method allows the chain elongation of peracetylated glyconic and glycuronic acids by the attachment of a polyprenyl or a related allyl residue. The reaction sequence leads to β,γ-unsaturated ketones 3 which may be converted to ketoses 4 by cleavage of the protecting groups. This technique permits the formal replacement of a hydrogen atom at the anomeric centre of a hexopyranose by a substituted allyl residue.
    Notes: Durch Ketenverlängerung mit Hilfe von C-Phenylglycin lassen sich peracetylierte Glycon-und Glycuronsäuren mit Polyprenyl- und anderen Allylresten verknüpfen. Man erhält die β,γ-ungesättigten Ketone 3, die nach Schutzgruppenabspaltung in die Ketosen 4 übergeführt werden können. Die Reaktionssequenz erlaubt damit den formalen Ersatz eines Wasserstoffatoms am anomeren Zentrum einer Hexopyranose durch einen substituierten Allylrest.
    Additional Material: 7 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198619860905
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  • 8
    Electronic Resource
    Electronic Resource
    Pilzfarbstoffe, 60 Über Leucomentine, farblose Vorstufen des Atromentins aus dem Samtfußkrempling (Paxillus atrotomentosus) (1989)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1989 (1989), S. 797-801 
    Details
    ISSN: 0170-2041
    Keywords: Terphenyl derivatives ; Leucomentins ; 2-Hexenoic acid, 4,5-epoxy- ; Paxillus atrotomentosus ; Atromentin, precursor of ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Fungal Pigments, 60. - Leucomentins, Colourless Precursors of Atromentin from the Mushroom Paxillus atrotomentosusAtromentin (1) occurs in sporophores of Paxillus atrotomentosus mainly in form of the colourless leucomentins 3-5. These compounds constitute esters of leucoatromentin with (2Z,4S,5S)-4,5-epoxy-2-hexenoic acid. The absolute configuration of the latter has been determined by its conversion into (+)-O-acetylosmundalactone (6a). The mechanism of the acid-catalyzed cleavage of the acyl residues has been studied by means of 18O labeling.
    Notes: Atromentin (1) liegt in Fruchtkörpern des Samtfußkremplings hauptsächlich in Form der farblosen Leucomentine 3-5 vor. Die Leucomentine sind Ester des Leukoatromentins mit (2Z,4S,5S)-4,5-Epoxy-2-hexensäure, deren absolute Konfiguration durch Überführung in (+)-O-Acetylosmundalacton (6a) bestimmt werden konnte. Dabei wurde der Mechanismus der säurekatalysierten Abspaltung der Säurereste durch 18O-Markierung aufgeklärt.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198919890227
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  • 9
    Electronic Resource
    Electronic Resource
    Pilzfarbstoffe, 61 Flavomentine und Spiromentine, neue Terphenylchinon-Derivate aus Paxillus atrotomentosus und P. panuoides (Boletales) (1989)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1989 (1989), S. 803-810 
    Details
    ISSN: 0170-2041
    Keywords: Fungal pigments ; Terphenylquinones ; Flavomentins ; Spiromentins ; Paxillus atrotomentosus ; Paxillus panuoides ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Fungal Pigments, 61. - Flavomentins and Spiromentins, Novel Terphenylquinone Derivatives from Paxillus atrotomentosus and P. panuoides (Boletales)The gilled toadstools Paxillus atrotomentosus and P. panuoides produce small amounts of orange-yellow flavomentins and violet spiromentins. The flavomentins 1-3 constitute mono- and diesters of atromentin (6) with (2Z,4E)-2,4-hexadienoic acid or (2Z,4S,5S)-4,5-epoxy-2-hexenoic acid. In addition, 3-O-acetylatromentin (4) has been isolated from P. atrotomentosu. The spiromentins 8,11,12, and 13 possess a unique spiro structure in which a 4,5-dihydroxy-1,2-benzoquinone is linked to a lactone acetal unit. The structures of the pigments were confirmed by the synthesis of model compounds and the biomimetic conversion of flavomentin B (2) into the spiromentins B (11) and C (12).
    Notes: Die Kremplinge Paxillus atrotomentosus und P. panuoides produzieren in geringen Mengen orangegelbe Flavomentine und violette Spiromentine. Bei den Flavomentinen 1-3 handelt es sich um Ester des Atromentins (6) mit (2Z,4E)-2,4-Hexadiensäure oder (2Z,4S,5S)-4,5-Epoxy-2-hexensäure, außerdem kommt als weitere Verbindung dieses Typs 3-O-Acetylatromentin (4) vor. Die Spiromentine 8, 11, 12 und 13 besitzen eine ungewöhnliche Spirostruktur, in der ein 4,5-Dihydroxy-1,2-benzochinon mit einem Lacton acetalartig verknüpft ist. Die spektroskopisch abgeleiteten Strukturen der Farbstoffe konnten durch die Synthese von Modellverbindungen und die biomimetische Überführung von Flavomentin B (2) in die Spiromentine B (11) und C (12) gesichert werden.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198919890228
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  • 10
    Electronic Resource
    Electronic Resource
    Komplexierung von Caesium-137 durch die Hutfarbstoffe des Maronenröhrlings (Xerocomus badius) (1989)
    Weinheim : Wiley-Blackwell
    Zeitschrift für die chemische Industrie 101 (1989), S. 495-496 
    Details
    ISSN: 0044-8249
    Keywords: Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/ange.19891010429
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