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  • 1
    Electronic Resource
    Electronic Resource
    Absolute Configuration of Multifidene and Viridiene, the Sperm Releasing and Attracting Pheromones of Brown AlgaePart V of a series; Part IV see [1]. (1983)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 66 (1983), S. 1905-1913 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The absolute configurations of the two algal pheromones multifidene 1 and viridiene 2 were determined as (+)-(3S, 4S)-3-[(Z)-1-butenyl]-4-vinylcyclopentene and (+)-(3R, 4S)-3-[(1Z)-1, 3-butadienyl]-4-vinylcyclopentene, respectively. The strategy involves enzyme-initiated asymmetric synthesis of the ring-saturated pheromone analogues (+)-8a and (-)-8b and their subsequent catalytic hydrogenation to the chiral cycloalkanes 9a and 9b, only the letter of which is also obtained from the two natural messengers (+)-1 or (+)-2. Biological activity assays proved these enantiomers of 1 or 2 to be the characteristic pheromones for male gametes of the seaweeds Syringoderma, Cutleria multifida and Chorda tomentosa.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19830660632
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  • 2
    Electronic Resource
    Electronic Resource
    Stereospezifische Synthese cis/trans-disubstituierter TetrahydrofuraneProf. Dr. Theodor Wieland zum 70. Geburtstag herzlich gewidmet (1983)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 66 (1983), S. 466-472 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Multifidene 1 is a chemical messenger for male gametes of the brown alga Cutleria multifida. The synthesis of messenger analogues with a tetrahydrofurane ring will be reported. The general synthetic approach offers the possibility to prepare a great variety of stereospecific 2,3- and 3,4-cis/trans-disubstituted tetrahydrofurans.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19830660207
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  • 3
    Electronic Resource
    Electronic Resource
    Synthetic routes to trace constituents of algal pheromone bouqets and other information-imitating substances (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 616-624 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Structural modifications of multifidene (1), viridiene (2) and ectocarpene (5) led to the synthesis of eleven new pheromone components or imitatin substances mostly by Grignard alkylation of cyclopentene and cycloheptadiene synthons. A new lactone α,ω dienol conversion is reported.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19840670230
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  • 4
    Electronic Resource
    Electronic Resource
    Synthesis of (±)-Desmarestene and (±)-Viridiene, the Two Sperm Releasing and Attracting Pheromones from the Brown Algae Desmarestia aculeata and Desmarestia viridis (1982)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 65 (1982), S. 2355-2362 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Desmarestene 1 6-(1Z,3-butadienyl)-1,4-cycloheptadiene and viridiene 3 cis-3-(1Z, 3-butadienyl)-4-vinylcyclopentene are chemical messengers for male gametes of the brown algae Desmarestia aculeate and Desmarestia viridis. Total syntheses of 1, 3 and their stereoisomers 1a, 3a-c are reported. Gas-chromatographic comparison of synthetic 1 and 3 with the corresponding natural products has established their structural identity.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19820650742
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  • 5
    Electronic Resource
    Electronic Resource
    Synthese und spektroskopische Eigenschaften pflanzlicher all-cis-Polyolefine (1981)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1981 (1981), S. 92-98 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis and Spectroscopic Properties of Plant all-cis-PolyolefinsPlant all-cis-polyolefins of the type 1a-c have been prepared by oxidative decarboxylation of the corresponding fatty acids or by synthesis starting with 1-chloro-4,7,10-tridecatriyne (5a) or 1-chloro-4,7-tridecadiyne (5b). Their spectroscopic properties are described.
    Notes: Pflanzliche all-cis-Polyolefine vom Typ 1a-c werden durch oxidative Decarboxylierung der entsprechenden Fettsäuren bzw. aus 1-Chlor-4,7,10-tridecatriin (5a) und 1-Chlor-4,7-tridecadiin (5b) synthetisiert. Ihre spektroskopischen Eigenschaften werden beschrieben.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198119810115
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  • 6
    Electronic Resource
    Electronic Resource
    Synthese und biologische Aktivitäten von (+)- und (-)-Multifiden (1981)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1981 (1981), S. 2266-2271 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis and Biological Activities of (+)- and (-)-Multifidene(+)-Multifiden 1, the specific messenger for androgametes of the phaeophyte Cutleria multifida, is about 100 times more active than the (-)-enantiomer of 1. Both enantiomers are conveniently prepared by chromatographic resolution of the diastereomeric carbamates 5a/b or 5c/d which give easy access to (+)- and (-)-1 by only a few subsequent steps.
    Notes: (+)-Multifiden 1, der spezifische Signalstoff für Androgameten der Braunalge Cutleria multifida, ist etwa 100fach wirksamer als das (-)-Enantiomere von 1. Die optische Reindarstellung beider Antipoden gelingt durch chromatographische Trennung der diastereomeren Carbamate 5a/b und 5c/d, aus denen (+)-und (-)-1 in nur wenigen Schritten zugänglich sind.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198119811214
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  • 7
    Electronic Resource
    Electronic Resource
    Synthese isomerer 1,3,5,8-Undecatetraene (1982)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1982 (1982), S. 579-584 
    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 Isomeric 1,3,5,8-Undecatetraenes(3E,5Z,8Z)-1,3,5,8-Undecatetraene (1a) is the smelling principle of the gametes of the brown alga Spermatochnus paradoxus. The synthesis of the isomeric 1,3,5,8-undecatetraenes 1a-c and their spectral properties are described.
    Notes: (3E,5Z,8Z)-1,3,5,8-Undecatetraen (1a) ist der Geruchsstoff von Gameten der Braunalge Spermatochnus paradoxus. Die Synthese der isomeren 1,3,5,8-Undecatetraene 1a-c und ihre spektroskopischen Eigenschaften werden beschrieben.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198219820318
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  • 8
    Electronic Resource
    Electronic Resource
    Studies in chemical ionization mass spectrometry: VFor part IV, see Ref. 1. - localization of homoconjugated triene and tetraene units in aliphatic compounds (1982)
    Chichester : Wiley-Blackwell
    Biological Mass Spectrometry 17 (1982), S. 161-164 
    Details
    ISSN: 0030-493X
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The homoconjugated triene (‘linolenic acid unsaturation’) and tetraene (‘arachidonic acid unsaturation’) pattern can be readily recognized and localized in aliphatic compounds by chemical ionization (NO) mass spectrometry. This method may be used for the screening of biological material, especially in food analysis.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/oms.1210170403
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  • 9
    Electronic Resource
    Electronic Resource
    Signalstoffe und ihre Reception im Sexualcyclus mariner Braunalgen (1982)
    Weinheim : Wiley-Blackwell
    Zeitschrift für die chemische Industrie 94 (1982), S. 659-670 
    Details
    ISSN: 0044-8249
    Keywords: Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Lockung und Schreck sind Antworten auf chemische Reize, die bereits von einzelligen Organismen ohne morphologisch abgegrenztes Nervensystem wahrgenommen und verarbeitet werden. Chemische Substanzen lösen Ereignisketten aus, die bei membrangebundenen Signalreceptoren beginnen und über regulierende und modulierende Glieder schließlich die Steuerung motorischer Erfolgsorgane bewirken. Untereinheiten dieser Receptoren werden durch die bindenden Signalstoffe in gegenseitiger Abhängigkeit konformativ verändert, chemisch modifiziert und in ihrer molekularen Aktivität beeinflußt. Dieses Wechselspiel führt, zusammen mit der eigentümlichen Motorik, zu einem zielgerichteten physiologischen Verhalten, durch das die begeißelten Geschlechtszellen (Gameten) mariner Braunalgen schließlich ihren Partner finden können. Die einfachen, aber jeweils hochspezifischen Systeme der Braunalgengameten wurden strukturell aufgeklärt und in ihrer biologischen Wirkung analysiert. Bei den Signalstoffen handelt es sich überwiegend um Monocyclen mit ungesättigten Seitenketten (Summenformel z. B. C11H14, C11H16, C11H18). Diese Systeme erleichtern als Modelle das Verständnis der komplexen Ganglienschaltungen bei höheren Lebewesen, in denen die Sinnesorgane über Nervenbahnen dem Zentralnervensystem Nachrichten aus der Umwelt übermitteln, die dort verarbeitet und, über ableitende Bahnen, durch den Bewegungsapparat beantwortet werden.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/ange.19820940902
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  • 10
    Electronic Resource
    Electronic Resource
    Signal Substances and their Reception in the Sexual Cycle of Marine Brown AlgaeDedicated to Professor Hermann Schildknecht on the occasion of his 60th birthday (1982)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 21 (1982), S. 643-653 
    Details
    ISSN: 0570-0833
    Keywords: Signal substances ; Brown algae ; Algae ; Pheromones ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Attraction and repulsion are responses to chemical stimuli which can be received and processed even by unicellular organisms without a morphologically defined nervous system. Chemical substances trigger off a chain of events which starts with a membrane-bound signal receptor and, after a sequence of regulatory and modulatory steps, ends in the modulation of a motor effector organ. Binding of the signal substances to the receptor produces conformational changes in which the receptor subunits are mutually dependent on one another, and also leads to chemical modification of the subunits and affects their molecular activity. These interactions, together with the characteristic type of movement, result in a physiological pattern of behavior which enables the flagellated sex cells (gametes) of marine brown algae to finally locate their partners. The simple but highly specific brown algae gamete systems have been investigated structurally and their biological activity analyzed. The signal substances are mainly highly unsaturated aliphatic or cyclic hydrocarbons with unsaturated side chains (general formula e. g. C11H14, C11H16, C11H18). These systems also serve as a simplifying model which helps in the understanding of complex ganglionic pathways in higher living organisms where the sense organs convey information from the surroundings to the central nervous system through nerve pathways. The information is then processed and answered, via efferent pathways, as movement.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/anie.198206433
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