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  • 11
    Electronic Resource
    Electronic Resource
    Revised Structure of the Fungal Germination Self-Inhibitor Gloeosporone (1987)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 70 (1987), S. 281-291 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Gloeosporone, the germination self-inhibitor from the fungus Colletotrichum gloeosporioides f.sp. jussiaea, is shown by spectroscopic data and X-ray analysis to have the constitution and relative configuration as shown in Formula 2 (either (1S,6R,12R)-1-hydroxy-6-pentyl-5,15-dioxabicyclo[10.2.1]pentadecan-4,13-dione or its enantiomer), rather than the previously assigned constitution 1.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19870700203
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  • 12
    Electronic Resource
    Electronic Resource
    Syntheses and X-Ray Structures for Model Compounds of a Pyrimidinediyl-Based Rigid-Rod Aromatic Polyamide (1992)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 75 (1992), S. 184-189 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A variety of model compounds for the pyrimidinediyl-based rigid-rod polyamide poly[imino-(pyrimidine-2,5-diyl)-imino-tetraphthaloyl] (PPYMT) was prepared, in order to compare their conformations to several model compounds of the related, fully aromatic polymer poly(p-phenyleneterephthalamide) (PPTA). In particular, the structures of N-(2-pyrimidyl)benzamide (PYMB) and its complexed form bis[(N-pyrimidin-2-yl)benzamide]nickel(II) dichloride (NiPYMB) were determined by X-ray diffraction. The molecular packing in these crystals provides us with a model for the possible ‘cross-linking’ of PPYMT fibers. The structures of the trimer model compounds N,N′ -bis(2-pyrimidyl)terephthalamide (PYTA) and N,N′ -bis(benzoyl)-2,5-diaminopyrimidine (BDAP) yield information about the conformation of PPYMT chains and are compared to analogous model compounds of PPTA.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19920750116
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  • 13
    Electronic Resource
    Electronic Resource
    Synthesis, Isolation, and NMR-Spectroscopic Characterization of Fourteen (Z)-Isomers of Lycopene and of Some Acetylenic Didehydro- and Tetradehydrolycopenes (1992)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 75 (1992), S. 1848-1865 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Eight (Z)-isomers of lycopene were prepared by stereocontrolled syntheses and fully characterized by 1H-NMR, 13C-NMR, mass, and UV/VIS spectroscopy: (5Z)-, (7Z)-, (15Z)-, (5Z,5′Z)-, (7Z,7′Z)-, (7Z,9Z)-, (9Z,9′Z)-, and (7Z,9Z,7′Z,9′Z)-lycopene. Six additional (Z)-isomers, namely (9Z)-, (13Z)-, (5Z,9′Z)-, (9Z,13′Z)-, (5Z,9Z,5′Z)-, and (5Z,13Z,5′Z)-lycopene, were isolated in small quantities from isomer mixtures by semiprep. HPLC and were identified by 1H-NMR spectroscopy.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19920750611
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  • 14
    Electronic Resource
    Electronic Resource
    Biosynthetic Production of [N2,1,3,7,9-15N]Guanosine and [1,3,7,9-15N]inosine and conversion into [N6,1,3,7,9-15N]adenosine for structure elucidation of RNA by heteronuclear NMR (1995)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 78 (1995), S. 421-439 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A procedure was developed for the biosynthetic preparation of 15N-labelled guanosine and inosine through the action of a mutant Bacillus subtilis strain. Crude [N2,1,3,7,9-15N]guanosine and [1,3,7,9-15N]inosine were isolated from the culture filtrate by precipitation and anion-exchange chromatography (Scheme 1). No cell lysis and no enzymatic degradation was necessary. The per-isobutyrylated derivatives 1 and 2 were isolated from a complex mixture, purified by virtue of their different lipophilicity, and separated in three steps involving normal-and reversed-phase silica-gel chromatography. One litre of complex nutrient medium yielded 8.44 mmol of guanosine derivative and 2.84 mmol of inosine derivative with high average 15N enrichment (83.5 and 91.9 atom-%, resp.). [N6,1,3,7,9-15N]Adenosine (4) was obtained from 2′,3′,5′-tri-O-isobutyryl[1,3,7,9-15N]inosine (1) through the ammonolysis of its 1,2,4-triazolyl derivative with aqueous 15NH3 (Scheme 2).
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19950780213
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  • 15
    Electronic Resource
    Electronic Resource
    Darstellung von 5-Hydroxy-1,7-naphthyridin (1979)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1979 (1979), S. 443-445 
    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 5-Hydroxy-1,7-naphthyridineN-(p-Toluenesulfonyl)glycine ester 1b reacts with 2-(bromomethyl)nicotinic ester 2 to form the nicotinic acid derivative 3b. Cyclization of 3b, by elimination of sulfinic acid, leads to the 1,7-naphthyridine derivative 7, from which the title compound 8 is formed.
    Notes: N-(p-Toluolsulfonyl)glycinester 1b reagiert mit 2-(Brommethyl)nicotinsäureester 2 zum Nicotinsäurederivat 3b. Dieses läßt sich unter Eliminierung von Sulfinsäure zum 1,7-Naphthyridin-derivat 7 cyclisieren, aus dem die im Titel genannte Verbindung 8 erhalten wird.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197919790402
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  • 16
    Electronic Resource
    Electronic Resource
    Synthesen von (-)-(S)- und (+)-(R)-Goniothalamin; absolute Konfiguration des natürlichen (+)-Goniothalamins (1979)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1979 (1979), S. 484-491 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Syntheses of (-)-(S)- and (+)-(R)-Goniothalamin; Absolute Configuration of the Naturally Occurring (+)-Goniothalamin(-)-(S)-Goniothalamin and its naturally occurring (+)-(R)-enantiometer were synthesised from configurationally defined precursors. The absolute configurations were additionally confirmed by ozonolysis to (-)-(S)- and (+)-(R)-malic acid. The absolute configuration given for the compound in the literature is thus corrected.
    Notes: (-)-(S)-Goniothalamin und das (+)-(R)-Enantiomer wurden aus konfigurativ definierten Vorstufen synthetisiert. Die absoluten Konfigurationen wurden zusätzlich durch Ozonabbau zu (-)-(S)- und (+)-(R)-Äpfelsäure bestätigt. Die in der Literatur angegebene absolute Konfiguration des Naturstoffs wird berichtigt.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197919790409
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  • 17
    Electronic Resource
    Electronic Resource
    Di- und Polyaminozucker, XXVIII1) Zur Substitution von 2-Amino-2-desoxy-α-D-glucopyranosiden in der 3-Stellung (1982)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1982 (1982), S. 265-274 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Di- and Polyamino Sugars, XXVIII1). - Substitution Reactions of 2-Amino-2-deoxy-α-D-gluco-pyranosides at Position 3Nucleophilic substitutions of N-protected 2-amino-2-deoxy-3-O-mesyl-α-D-glucopyranosides with azide ions were severely restricted by neighboring group participations. N-acetyl as blocking group (2) led to the formation of the oxazoline 3 while from N-dinitrophenyl derivatives (9; 17) isomeric products (10, 11; 18, 19) were formed via epimines. Structure proofs were given by spectroscopy as well as by independent syntheses.
    Notes: Nucleophile Substitutionen an N-geschützten 2-Amino-2-desoxy-3-O-mesyl-α-D-glucopyranosiden mit Azid-Ionen wurden durch Nachbargruppenreaktionen behindert. N-Acetyl als Schutz-gruppe (2) führte zum Oxazolin 3, aus Dinitrophenyl-Derivaten (9; 17) wurden über Epimine isomere Produkte (10, 11; 18, 19) erhalten. Die Konstitutionsbeweise wurden sowohl anhand der Spektren als auch durch unabhängige Synthesen geführt.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198219820210
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  • 18
    Electronic Resource
    Electronic Resource
    Zuckertosylate via p-Toluolsulfinsäureester. p-Toluolsulfinimidazolid als Reagenz zur halogenidfreien Sulfinesterbildung (1981)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1981 (1981), S. 1354-1360 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Sugar Tosylates via p-Toluenesulfinic Acid Esters.  -  p-Toluenesulfinimidazolide  -  A Reagent for Formation of Sulfinic Acid Esters without Using HalidesThe reaction of the protected sugar derivatives 1, 4, 7, 10, 13, 16, 19 and 20 with p-toluenesulfin-imidazolide prepared from p-toluenesulfinic acid and N,N'-carbonyldiimidazole yields the corresponding p-toluenesulfinic esters 2, 5, 8, 11, 14, 17, 20 and 22. With the exception of 20 and 22, these products can be oxidized with m-chloroperbenzoic acid in high yields and short overall reaction times to the tosylates 3, 6, 9, 12, 15 and 18.
    Notes: Durch Umsetzung der blockierten Zuckerderivate 1, 4, 7, 10, 13, 16, 19 und 21 mit dem aus p-Toluolsulfinsäure und N,N'-Carbonyldiimidazol intermediär gebildeten p-Toluolsulfinimidazolid werden die p-Toluolsulfinsäureester 2, 5, 8, 11, 14, 17, 20 und 22 erhalten. Daraus lassen sich mit Ausnahme von 20 und 22 in hohen Ausbeuten und insgesamt kurzer Reaktionszeit die entsprechenden Tosylate 3, 6, 9, 12, 15 und 18 durch Oxidation mit m-Chlorperbenzoesäure darstellen.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198119810803
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  • 19
    Electronic Resource
    Electronic Resource
    Methyl-2,5 : 3,6-dianhydro-D-mannofuranoside (1983)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1983 (1983), S. 1345-1353 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Methyl 2,5:3,6-Dianhydro-D-mannofuranosidesMonotosylation of methyl 3,6-anhydro-β-D-glucofuranoside gives as minor reaction product 1 which yields by treatment with sodium ethanolate methyl 2,5 : 3,6-dianhydro-β-D-mannofuranoside (2). The α-anomer 6 is equally prepared from 3 which is obtained by selective monotosylation of methyl 3,6-anhydro-β-L-gulofuranoside. Reaction of methyl 3,6-anhydro-2,5-di-O-tosyl-α-D-glucofuranoside (5) gives only small amounts of 6 accompanied by the monotosylate 4. Mass and NMR spectra (2D-1H and 13C) of the new dianhydrides 2 and 6 are described.
    Notes: Monotosylierung von Methyl-3,6-anhydro-bT-D-glucofuranosid ergibt als Nebenprodukt 1, dessen Behandlung mit Natrium-ethanolat zum Methyl-2,5 : 3,6-dianhydro-β-D-mannofuranosid (2) führt. Das entsprechende α-Anomere 6 kann analog aus 3, dem Produkt der selektiven Monotosylierung des Methyl-3,6-anhydro-β-L-gulofuranosids erhalten werden. Hingegen liefert die Umsetzung des Methyl-3,6-anhydro-2,5-di-O-tosyl-α-D-glucofuranosids (5) nur geringe Mengen 6 neben Monotosylat 4. Die NMR-Spektren (2D-1H und 13C) sowie der massenspektrometrische Zerfall der neuen Dianhydride 2 und 6 werden beschrieben.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198319830807
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  • 20
    Electronic Resource
    Electronic Resource
    Dihydropyridine, VI. Diimidomalonsäurederivate in der Hantzsch-Pyridin-SyntheseHerrn Prof. Dr. Herbert Grünewald zum 60. Geburtstag gewidmet. (1981)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1981 (1981), S. 1523-1533 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Dihydropyridines, VI1).  -  Derivatives of Diimido Malonic Acid in the Hantzsch Pyridine SynthesisOne-pot-condensation of aldehydes 6, 2,2′-methylenediimidazoline hydrochloride (7) and β-dicarbonyl compounds 10 leads to 1,2,3,7-tetrahydro-8-(2-imidazoline-2-yl)imidazo[1,2-a]pyridine hydrochloride 11. Michael addition of 7 to α,β-unsaturated ketones is followed by ring closure to give 16, 17, and 18. Condensation of the free base 8a with aldehydes 6 and 1,3-cyclohexanedione yields the fused imidazopyridines 19a-d. Compounds 20 and 21 are prepared by use of a second enamine in the one-pot-synthesis, thus furnishing another basic centre. 2,2′-Methylenedi(2-thiazoline) hydrochloride (22) is prepared by condensation of diethyl malonodiimidate and 2-amino
    Notes: Die Dreikomponenten-Kondensation von Aldehyden 6, 2,2′-Methylendiimidazolin-hydrochlorid (7) und β-Dicarbonylverbindungen 10 führt zu 1,2,3,7-Tetrahydro-8-(2-imidazolin-2-yl)imidazo-[1,2-a]pyridin-hydrochloriden 11. Die Verbindungen 16, 17 und 18 werden durch cyclisierende Michael-Addition von 7 an α,β-ungesättigte Ketone erhalten. Die freie Base 8a kondensiert mit 1,3-Cyclohexandion und den Aldehyden 6 zu den anellierten Imidazopyridinen 19a-d. Einsatz eines zweiten Enamins in der Dreikomponenten-Reaktion liefert die Verbindungen 20 und 21 mit einem weiteren basischen Zentrum. 2,2′-Methylendi(2-thiazolin)-hydrochlorid (22) wird durch Kondensation von Malondiimidsäure-diethylester und 2-Aminoethanthiol-hydrochlorid erhalten. Natronlauge liefert die freie Base 8b. Die 2,3-Dihydro-8-(2-thiazolin-2-yl) 7H-thiazolo[3,2-a]-pyridine 23, 25, 26, 28 und 29 sind durch cyclisierende Michael-Addition von 8b an verschiedene α,β-ungesättigte Carbonylverbindungen in Ethanol oder Eisessig zugänglich.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198119810902
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