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  • Life and Medical Sciences  (96)
  • Natural products  (22)
  • Biochemistry and Biotechnology
  • Physics
  • Wiley-Blackwell  (118)
  • 1995-1999  (118)
  • 1940-1944
  • 1999  (118)
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  • 1995-1999  (118)
  • 1940-1944
Year
  • 1
    Electronic Resource
    Electronic Resource
    2D-NMR-Guided Constitutional Analysis of Organic Compounds Employing the Computer Program COCON[#] (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 573-577 
    Details
    ISSN: 1434-193X
    Keywords: Structure elucidation ; Constitutional analysis ; Natural products ; HMBC ; Computational chemistry ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The computer program COCON is introduced as a tool for the comprehensive structure elucidation of unknown organic compounds. In particular, structural proposals made on the basis of the molecular formula and of 2D-NMR experiments can be analyzed for the existence of alternative constitutions being in agreement with the same data set. The computational speed grounds on the evaluation of ambiguous long-range connectivity information during the process of structure generation. The data set experimentally obtained for the marine natural product oroidin (1) was selected, because proton-poor compounds usually cause uncertainties in NMR-based structure determinations. The calculation results encourage to move from the experience-based analysis of NMR chemical shifts or of MS fragmentations to the automated evaluation of routinely available connectivity information.Supporting information for this article is available on the WWW under -http://www.wileY-Vch.de/contents/jc_2046/1999/98241_s.pdf or from the author.
    Additional Material: 6 Ill.
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  • 2
    Electronic Resource
    Electronic Resource
    Radical Cyclizations - Synthesis of γ-Lycorane (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 1925-1933 
    Details
    ISSN: 1434-193X
    Keywords: γ-Lycorane ; Radicals ; Cyclizations ; Natural products ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: (±)-γ-Lycorane has been synthesized in ten steps from piperonylic alcohol. Two radical reactions were used successively to build the D and B rings. A formal synthesis of (+)-γ-lycorane was achieved via an optically active unsaturated aldehyde intermediate.
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  • 3
    Electronic Resource
    Electronic Resource
    A Chiral β,δ-Dioxo-ε-sulfinyl Ester in a Convergent Enantioselective Synthesis towards the C1-C13 Polyol Fragment of Amphotericin B (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 3021-3026 
    Details
    ISSN: 1434-193X
    Keywords: Natural products ; Antibiotics ; Macrolides ; Asymmetric synthesis ; Chiral sulfoxide ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: This paper describes an efficient stereocontrolled and convergent approach towards the C1-C13 polyol fragment of amphotericin B. The strategy is based on the stereoselective reduction of a chiral β,γ-dioxo-ε-sulfinyl ester to obtain anti- or syn-1,3-diols.
    Additional Material: 1 Ill.
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  • 4
    Electronic Resource
    Electronic Resource
    A COCON Analysis of Proton-Poor Heterocycles - Application ofCarbon Chemical Shift Predictions for the Evaluation of Structural Proposals (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 579-586 
    Details
    ISSN: 1434-193X
    Keywords: Structure elucidation ; Computational method ; Natural products ; HMBC ; Constitutional analysis ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The application of the new computer program COCON (Constitutions from Connectivities) to the 2D-NMR data sets of three different complex natural products is described. The investigated compounds are proton-poor and therefore underdetermined systems. For such molecules the number of possible constitutions and the computational speed of COCON are of interest. Our investigation is focused on how methods of 13C-NMR chemical shift prediction can assist chemists with regard to refining the selection among the constitutions proposed by COCON.
    Additional Material: 6 Ill.
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  • 5
    Electronic Resource
    Electronic Resource
    Synthesis of rac-(E)-Opposita-4(15),7(11)-dien-12-al (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 675-678 
    Details
    ISSN: 1434-193X
    Keywords: rac-(E)-Opposita-4(15),7(11)-dien-12-al ; Natural products ; Vetiver oil ; Octahydroindene derivatives ; Fragrances ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -rac-(E)-Opposita-4(15),7(11)-dien-12-al (1) was synthesized in 12 steps via the aldehyde 11 as the key compound. The spectroscopic data of rac-1 are identical with those of the corresponding natural product, previously isolated from Vetiver oil. Synthetic rac-1 has a strong, green woody odor with soft-floral undertones, which confirms that 1 is an olfactorily important constituent of Vetiver oil.
    Additional Material: 1 Tab.
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  • 6
    Electronic Resource
    Electronic Resource
    Isolation and Structural Elucidation of Crellastatins B-H: Cytotoxic Bis(steroid) Derivatives from the Vanuatu Marine Sponge Crella sp. (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 949-953 
    Details
    ISSN: 1434-193X
    Keywords: Natural products ; Dimeric steroids ; Crellastatins ; Sponge ; Crella sp. ; 2D NMR ; Antitumor agents ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Seven new cytotoxic dimeric steroids, namely crellastatins B-H (2-8), have been isolated from the Vanuatu sponge Crella sp. They have been structurally characterized on the basis of 2D-NMR (500 MHz) and FAB-MS data. All the new compounds show the same unprecedented junction between the monomeric units, formed via their side-chains, whereas they differ from A (1) in the hydroxylation pattern of the two tetracyclic cores. Like crellastatin A (1), crellastatins B-H (2-8) exhibit in vitro antitumor activity against human bronchopulmonary non-small-cell lung carcinoma cell lines (NSCLC) with IC50 values in the range of 2-10 μg/mL.
    Additional Material: 4 Ill.
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  • 7
    Electronic Resource
    Electronic Resource
    Metabolites from the Wood-Rotting Basidiomycete Hapalopilusmutans (Aphyllophorales) (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 1051-1055 
    Details
    ISSN: 1434-193X
    Keywords: Fungus ; Dihydroxybenzoic acids ; Benzoquinones ; Spirodiones ; Natural products ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Fruit bodies of the wood-rotting North American fungus Hapalopilusmutans produce a mixture of dihydroxybenzoic acids 1, dihydroxybenzoquinones 2 and a novel type of spirodiones, e.g. mutadione A (4a). All compounds carry long alkyl chains, which may be partially unsaturated. The structures of the metabolites were established by spectroscopic methods.
    Additional Material: 4 Ill.
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  • 8
    Electronic Resource
    Electronic Resource
    EPC Syntheses of Trifluorocitronellol and of Hexafluoropyrenophorin - A Comparison of Their Physiological Properties with the Nonfluorinated Analogs (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 2533-2544 
    Details
    ISSN: 1434-193X
    Keywords: (S)-4,4,4-Trifluoro-3-hydroxybutanoic acid ; 2-Trifluoromethyl-3-hydroxypropanoic acid (F3-Roche acid) ; Chiral CF3-containing synthetic building blocks ; Natural products ; Cyclizations ; Olfactory comparison ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The natural products pyrenophorin (1a) and citronellol (2a), in which CH3 groups are replaced by CF3, were synthesized in enantiomerically pure form from simple four-carbon trifluorohydroxy acids (obtained by resolution). The cyclizations of analogous CH3 and CF3 seco acids (cf. 9) to give pyrenophorin derivatives require different methodologies; the F6 derivative 10a could be obtained in only very poor yield; in contrast to pyrenophorin. Most surprisingly, F6-pyrenophorin (1d) has an extremely poor solubility in common organic solvents, and has essentially no antimicrobial activity (see Table 2). The synthesis of F3-citronellol is the first application of an enantiopure F3-Roche acid (12) as a synthetic builiding block (see its derivatives 17-23). An olfactory comparison of F3-citronellol [(R)-(+)-2b] with citronellol and ent-citronellol (Scheme 6) shows that the fluorine derivative has a “very metallic, aggressive” character and lacks totally the “sweetness” of (R)-(+)- and (S)-(-)-2a. A number of generally useful, CF3-substituted electrophilic (iodides 4, 18, 37, tosylates 19, 33, aldehydes 5, 29, 39) and nucleophilic (Li dithiane precursor of 5, Li compounds 20, 38) reagents are described for the first time.Supporting information for this article is available on the WWW under //http://www.wiley-vch.de/contents/jc_2046/1999/99137_s.pdf or from the author.
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  • 9
    Electronic Resource
    Electronic Resource
    A New Tyrosine Kinase Inhibitor from a Marine Isolate of Ulocladium botrytis and New Metabolites from the Marine Fungi Asteromyces cruciatus and Varicosporina ramulosa (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 2949-2955 
    Details
    ISSN: 1434-193X
    Keywords: Marine fungi ; Tyrosine kinase ; Natural products ; Macrodiolides ; Polyketides ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The sponge-derived fungi Ulocladium botrytis and Asteromyces cruciatus, and the algal-derived fungus Varicosporina ramulosa, were isolated and extracts from cultures investigated for their metabolite production. Investigations of the extract of the culture of U. botrytis guided by bioassay yielded the new tyrosine kinase (p56lck) inhibitor ulocladol (1) together with 1-hydroxy-6-methyl-8-(hydroxymethyl)xanthone (3), which showed antifungal activity. The extract of the culture medium of A. cruciatus yielded the new metabolite (+)-2,4-dimethyl-4,5-dihydrofuran-3-carbaldehyde (4) together with the known compounds (3S,5R)-dimethyldihydrofuran-2-one (5) and tri-O-acetyl glycerol. From V. ramulosa the five macrodiolides grahamimycin A1 (6), colletoketol (7), (6R,11R,12R,14R)-colletodiol (8), 9,10-dihydro-(6R,11S,12S,14R)-colletodiol (9) and 9,10-dihydro-(6R,11R,12R,14R)-colletodiol (10) together with ergosterol were obtained, 9 and 10 being new fungal metabolites.
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  • 10
    Electronic Resource
    Electronic Resource
    Structure of Neuritogenic Active Ganglioside from the Sea Cucumber   Stichopus japonicus (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 3171-3174 
    Details
    ISSN: 1434-193X
    Keywords: Glycosphingolipid ; Ganglioside ; Sea cucumber ; Stichopus japonicus ; Neuritogenic activity ; Natural products ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A ganglioside molecular species SJG-1 has been obtained from the n-hexane soluble lipid fraction of the chloroform/methanol extract of the sea cucumber Stichopus japonicus. On the basis of chemical and spectroscopic evidence, the structure of SJG-1 has been determined. SJG-1 possesses an N-glycolylneuraminic acid (sialic acid), nonhydroxy fatty acids and phytosphingosine-type long-chain bases as major ceramide components. The ganglioside SJG-1 exhibits neuritogenic activity toward the rat pheochromocytoma cell line PC12 cells in the presence of NGF.
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