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  • Organic Chemistry  (5)
  • 2015-2019
  • 1985-1989  (5)
  • 1
    Electronic Resource
    Electronic Resource
    Cyclization Reactions with Allyl-Substituted Glucose Derivatives (1987)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1987 (1987), S. 731-732 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The 3-Allyl-3-deoxyglucosyl radical 8a cyclizes with high diastereoselectivity to give bicyclic dideoxysugars 7a and 7b, whereas the 6-allyl-6-deoxyglucosyl radical does not give cyclized products. This proves the boat conformation of 2a for glucosyl radicals.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198719870820
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  • 2
    Electronic Resource
    Electronic Resource
    Synthesis of 2-deoxy sugars (1988)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1988 (1988), S. 615-617 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The reduction of acetylated or benzoylated glycosyl halides or selenides with low concentrations of tributylstannane leads to 2-deoxy sugars. An important step in this radical-chain reaction is the cis-selective migration of an ester group. The broad applicability of this method is demonstrated by the synthesis of mono- and dideoxy sugars, of α- and β-deoxy sugars, of deoxypyranoses and deoxyfuranoses, of deoxypentosyl- and -hexosyl carbohydrates.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198819880625
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  • 3
    Electronic Resource
    Electronic Resource
    Dimerization of carbohydrate radicals (1988)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1988 (1988), S. 997-1000 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Glycosyl bramides and selenides 1 react with hexamethylditin to give coupling products 2-4 in 32% yield. The reactions occur by dimerization of glycosyl radicals, the radical 8 in the 4C1 chair conformation being slightly more stereoselective than the glucosyl radical 7 in the B2,5 boat conformation.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198819881012
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  • 4
    Electronic Resource
    Electronic Resource
    Synthesis of Pheromones with Acetal Structures via Radical C—C Bond Formation (1987)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1987 (1987), S. 427-429 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthese von Pheromonen mit Acetalstrukturen über radikalische C—C-BindungsbildungDie spirocyclischen Acetale 4a, 4b und exo-Brevicomin (5) werden als Racemate durch radikalische Additionen an Divinylketon bzw. Methylvinylketon synthetisiert. Radikalvorläufer sind das Alkylquecksilbersalz 6 bzw. die Iodide 9a,9b, die durch Solvomercurierung von Propen bzw. 1-Penten-3-ol (8) hergestellt werden. Reduktion der Ketongruppen unter den reduzierenden Bedingungen der Radikalkettenreaktionen wurde nicht beobachtet.
    Notes: Spirocyclic acetals 4a, 4b and exo-brevicomin (5) are synthesized as racemates via radical additions to divinyl ketone and methyl vinyl ketone, respectively. Radical precursors are the alkyl mercuric salt 6 and iodides 9a,9b, which can easily be generated via solvomercuration of propene and 1-penten-3-ol (8), respectively. Reduction of the ketone groups under the reducing conditions of these radical chain reactions was not observed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198719870348
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  • 5
    Electronic Resource
    Electronic Resource
    Total Synthesis of (-)-Malyngolide and of Its Three Stereomers (1987)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1987 (1987), S. 231-233 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Totalsynthese von (-)-Malyngolid und seinen drei Stereomeren(-)-Malyngolid (1a) und seine drei Stereomeren 1b-d werden aus dem Allylalkohol 4 in jeweils 10% Gesamtausbeute synthetisiert. Schlüsselstufen der Synthese sind die Sharpless-Epoxidierung des Allylalkohols 4 und die radikalische C—C-Bindungsbildung mit dem Iodid 3 und Methacrylsäure-methylester (2). Diese radikalische C—C-Bindungsbildung benötigt nur geringe Mengen an Organozinnverbindungen.
    Notes: (-)-Malyngolide (1a) and its three stereomers 1b-d are synthesized from the allylic alcohol 4 in total yields of about 10% each. The key reaction steps are Sharpless epoxidation of the allylic alcohol 4 and radical C—C bond formation with the iodide 3 and methyl methacrylate (2). This radical chain reaction needs only small amounts of organotin compounds.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198719870313
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