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  • Chemistry  (46)
  • Cyclodextrin derivatives  (5)
  • cyclodextrin derivatives  (5)
  • Cyclodextrins  (2)
  • Polychlorinated pesticides  (2)
  • 2,8-dimethyl-1,7-dioxaspiro[5.5]undecane  (1)
  • 1995-1999  (13)
  • 1990-1994  (34)
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Keywords
Publisher
Years
Year
  • 1
    Electronic Resource
    Electronic Resource
    Andrena wilkella male bees discriminate between enantiomers of cephalic secretion components (1990)
    Springer
    Journal of chemical ecology 16 (1990), S. 429-441 
    Details
    ISSN: 1573-1561
    Keywords: Enantiomer discrimination ; male patrolling ; odor marking ; Hymenoptera ; Apoidea ; Andrena wilkella ; bee ; EAG ; spiroacetal ; absolute configuration ; 2,8-dimethyl-1,7-dioxaspiro[5.5]undecane
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Diastereomers of the spiroacetal, 2,8-dimethyl-1,7-dioxaspiro [5.5]undecane, represent main components of the cephalic secretion from males of the solitary bee,Andrena wilkella. The major compound proved to be of high enantiomeric purity, showing (2S,6R,8S) configuration. Only the naturally occurring enantiomer attracted patrolling males in the field; its antipode was behaviorally inactive and in a racemic mixture did not inhibit response. The (E,Z) diastereomers were also found to be almost inactive. EAG studies gave the same result as the behavioral tests. The biological function of the spiroacetal is discussed in view of the evolution of the mating behavior inA. wilkella.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01021775
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  • 2
    Electronic Resource
    Electronic Resource
    Unusual and Novel C11H16 Hydrocarbons from the Southern Australian Brown Alga Dictyopteris acrostichoides (Phaeophyceae) (1992)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 75 (1992), S. 734-744 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Unusual and novel C11H16 olefins with (E)- or (E,E)-configuration instead of the previously known (Z)- or (E,Z)-configuration at the double bond(s) within the longer side chain are the main products of the Australian phaeophyte Dictyopteris acrostichoides. This configuration anomaly refers to all four series of alicyclic C11H16 hydrocarbons, namely the disubstituted cyclopentenes and cyclopropanes, as well as the monosubstituted cycloheptadienes and cyclopentenes. Chiral compounds within the above series have the same absolute configuration. The two (cyclopent-3-enyl)hexa-1, 3-dienes 11 and 13 are found for the first time. The absolute configuration and optical purity of the hydrocarbons are determined by gas chromatography on modified cyclodextrins as chiral stationary phases. The synthesis of chiral references via lipase-catalyzed resolutions is described.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19920750309
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  • 3
    Electronic Resource
    Electronic Resource
    Synthesis and Absolute Configuration of the C12-Terpenoid Dehydrogeosmin from the Flower Scents of Rebutia marsoneri and Dolichothele sphaerica (Cactaceae); a new approach to bis-angularly substituted trans-decalins (1993)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 76 (1993), S. 1949-1955 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Optically pure(+)-(4S, 4aS, 8aS)-1,2,3,4,4a,5,8,8a-octahydro-4,8a-dimethylnaphthalen-4a-ol((+)-1; dehydrogeosmin) is released from flower heads of the two cactaceae Rebutia marsoneri and Dolichothele spharica. The absolute configuration of (+)-1 is identical with that of the known microbial metabolial geosmin (-)-2. The key reactions of the synthesis of 1 are the kinetically controlled transesterification of the primary alcohol 4 using a lipase from Candida cyclindracea and the stereo-and regiospecific angular alkylation of a cis-decalin skeleton by a Lewis-acid-assisted ring opening of the quaternary epoxy-alcohol 3 with MeMgBr/Cul. The sequence provides a new entry into the class of bis-angularly substituted trans-decalins.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19930760513
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  • 4
    Electronic Resource
    Electronic Resource
    Separation of Enantiomeric Irones by Gas-Liquid Chromatography on Modified Cyclodextrins (1990)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 73 (1990), S. 2165-2170 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Natural irones found in the essential oil of Iris rhizomes often are mixtures of enantiomers. The separation of all optical isomers of the irones by GLC on modified cyclodextrins and the determination of their composition within different Iris oils is described. The significance for the biosynthesis of the cycloiridals, C31-triterpenoids, which serve as precursors of the irones, is discussed.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19900730812
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  • 5
    Electronic Resource
    Electronic Resource
    Zum Mechanismus der Cyclopropan-“Walk”-Umlagerung: Synthese und Eigenschaften eines optisch aktiven Diazoalkan-Addukts von Toluol; eine hochstereoselektive N2-EliminierungHerrn Professor Horst Prinzbach zum 60. Geburtstag gewidmet. (1992)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 125 (1992), S. 197-208 
    Details
    ISSN: 0009-2940
    Keywords: Azoles, optically active, thermolysis and photolysis of ; Walk rearrangement ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Mechanism of the Cyclopropane “Walk” Rearrangement: Synthesis and Properties of an Optically Active Diazoalkane-Toluene Adduct; a Highly Stereoselective N2 EliminationThe synthesis and the thermal and photochemical behavior of the optically active 2-diazo-1-methoxypropane-toluene adduct 3 are reported. The N2 elimination of 3 ocurs with one and the same stereochemical course upon thermolysis as well as direct photolysis: 7-(Methoxymethyl)-1,7-dimethyl-1,3,5-cycloheptatriene (1) is formed with retention of configuration at C-7 and 7-(methoxymethyl)-2,7-dimethyl-1,3,5-cycloheptatriene (2) with inversion of configuration at C-7. These stereochemical findings are explained by an intermediary singlet diradical 1[4] in which the ring closure between C-1 and C-7 or C-5 and C-7 is faster than the rotation around the single bond between C-6 and C-7. In the case of the thermally induced formation of 2 a concerted N2 elimination has to be considered as a competitive pathway. The results presented here are well in accord with the stereochemical analysis of the cyclopropane “walk” rearrangement 1⇋2 reported previously and are therefore a good evidence that the diradical intermediate 4 is also involved in the “walk” rearrangement. In the photochemically induced N2 elimination of 3, sensitized by benzophenone and leading again to 1 and 2, a surprisingly high degree of stereoselectivity is observed. Thus, the intermediary triplet diradical 3[4] must have a much shorter life time than ordinary 1,3-diradicals in the triplet state.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19921250132
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  • 6
    Electronic Resource
    Electronic Resource
    Neue optisch aktive Chelat-Phosphane - Synthese und Verwendung in der enantioselektive Katalyse (1990)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 123 (1990), S. 847-853 
    Details
    ISSN: 0009-2940
    Keywords: Phosphines, optically active / Nickel complexes / Hydrogenation, enantioselective / Grignard cross coupling, enantinoselective / Gas chromatography, enantioselective ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Asymmetric Catalysis, LI. - New Optically Active Chelating Phosphines - Synthesis and Application in Enantioselective CatalysisThe known triphosphines 1 and 4 were transformed into their monophosphine oxide and monophosphine sulfide derivatives 2, 3, 5, and 6 via NiCl2 complexes. 21 optically active phosphines were used as ligands in the Rh-catalysed hydrogenation of (Z)-α-acetamidocinnamic acid and itaconic acid as well as in the Ni-catalysed cross-coupling reaction of phenylethylmagnesium chloride with vinyl bromide. The optical inductions of the Grignard cross coupling reaction were determined the first time by enantioselective gas chromatography.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19901230433
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  • 7
    Electronic Resource
    Electronic Resource
    A Molecular-Dynamics Simulation of the Complex Formation between Methyl (R)/(S)-2-Chloropropionate and Heptakis(3-O-acetyl-2,6-di-O-pentyl)-β-cyclodextrin (1994)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 127 (1994), S. 119-126 
    Details
    ISSN: 0009-2940
    Keywords: Host-guest complexes ; Molecular-dynamics (MD) simulation ; Enantioselective gas chromatography ; Cyclodextrins ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The energies of complexation of methyl (R)/(S)-2-chloropropionate [(R)/(S)-2] with heptakis(3-O-acetyl-2,6-di-O-pentyl)-β-cyclodextrin (1) and the structures of the corresponding complexes were determined by molecular-dynamcis (MD) simulations at 300 and 333 K. The geometry of the complexes, the conformations of complexed and uncomplexed 1 and (R)/(S)-2 and the closest H-H distances between host and guest in the complexes were determined from the trajectories. The results correspond to the experimental findings from enantioselective gas chromatography.
    Additional Material: 9 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19941270120
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  • 8
    Electronic Resource
    Electronic Resource
    Enantioselective and nonenantioselective degradation of organic pollutants in the marine ecosystem (1993)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 5 (1993), S. 393-399 
    Details
    ISSN: 0899-0042
    Keywords: chiral capillary gas chromatography ; chiral high-performance liquid chromatography ; stationary cyclodextrin phases ; chiral pollutants ; enantioselective processes ; microbial degradation processes ; photochemical degradation processes ; enzymatic degradation processes ; blood-brain barrier ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Enantiomeric ratios of 11 chiral environmental pollutants determined in different compartments of the marine ecosystem by chiral capillary gas chromatography and chiral high-performance liquid chromatography allow discrimination between the following processes: enantioselective decomposition of both enantiomers with different velocities by marine microorganisms (α-HCH, β-PCCH, γ-PCCH); enantioselective decomposition of one enantiomer only by marine microorganisms (DCPP); enantioselective decomposition by enzymatic processes in marine biota (α-HCH, β-PCCH, trans-chlordane, cis-chlordane, octachlordane MC4, octachlordane MC5, octachlordane MC7, oxychlordane, heptachlor epoxide); enantioselective active transport through the “blood-brain barrier” (α-HCH); nonenantioselective photochemical degradation (α-HCH, β-PCCH). © 1993 Wiley-Liss, Inc.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530050522
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  • 9
    Electronic Resource
    Electronic Resource
    Determination of the enantiomeric composition of mexiletine and its four hydroxylated metabolites in urine by enantioselective capillary gas chromatography (1996)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 8 (1996), S. 30-34 
    Details
    ISSN: 0899-0042
    Keywords: gas chromatography ; modified β-cyclodextrin column ; chiral separation ; assay ; mexiletine ; hydroxylated metabolites ; urine ; conjugation/deconjugation ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The enantiomers of mexiletine and four of its hydroxylated metabolites were directly separated by capillary gas chromatography using a heptakis(6-O-tert-butyl-dimethylsilyl-2,3-di-O-methyl)-β-cyclodextrin column. The method was applied to the analysis of urine samples from cancer patients who were treated with racemic mexiletine as part of a study of the use of mexiletine in the relief of neuropathic pain. Samples analyzed before and after deconjugation of the urine with β-glucuronidase/arylsulfatase showed a high stereoselectivity in the formation and conjugation of these compounds. © 1996 Wiley-Liss, Inc.
    Additional Material: 3 Ill.
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  • 10
    Electronic Resource
    Electronic Resource
    Enantioselective capillary gas chromatography in the investigation of stereochemical correlations of terpenoids (1998)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 10 (1998), S. 499-504 
    Details
    ISSN: 0899-0042
    Keywords: enantioselective capillary gas chromatography ; cyclodextrin derivatives ; stereochemistry of terpenes ; monoterpenes ; essential oils ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Capillary gas chromatography employing the unique selectivities of specifically substituted cyclodextrins is highly suited for stereochemical investigations of terpenoid compounds. The analysis of many essential oils have shown that monoterpene derivatives regularly occur as enantiomeric mixtures. In the case of sesquiterpene hydrocarbons, liverworts (Hepaticae) and other lower organisms usually biosynthesize compounds of opposite stereochemistry as compared to higher plants and enantiomeric mixtures occur only occasionally. The investigation of diterpene hydrocarbons has so far shown no indication of the presence of both enantiomers in the same plant. Chirality 10:499-504, 1998. © 1998 Wiley-Liss, Inc.
    Additional Material: 7 Ill.
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