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  • Fluorine  (2)
  • 1
    Electronic Resource
    Electronic Resource
    Synthesis of Enantiomerically Pure 2′,3′,5′-Trideoxy-4′-[(diethoxyphosphoryl)difluoromethyl]thymidine Analogues (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 2149-2157 
    Details
    ISSN: 1434-193X
    Keywords: Fluorine ; Sulfoxides ; Nucleotide analogues ; Asymmetric synthesis ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: D- and L-(diethoxyphosphoryl)difluoromethyl nucleoside analogues 10 have been synthesized using the building block approach, starting from chiral fluorinated molecules. The key steps of the synthetic sequence were condensation of 2-methyl-5-(4-methylphenylsulfinyl)pent-2-ene (1) and ethyl 2-(diethoxyphosphoryl)-2,2-difluoroacetate (2), reduction of the thus formed ketones 3 to alcohols 4, reductive removal of the sulfur moiety to give hydroxy phosphonates 6, and oxidative cyclization to give furanose derivatives 8.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
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    Paper (German National Licenses)
  • 2
    Electronic Resource
    Electronic Resource
    Synthesis of 2-Fluoro Analogues of Frontalin (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 1387-1389 
    Details
    ISSN: 1434-193X
    Keywords: Natural products ; Epoxidations ; Asymmetric synthesis ; Fluorine ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---The synthesis of enantiomerically and diastereomerically pure (-)-(1R,2R,5R)- and (-)-(1R,2S,5R)-2-fluoro frontalin (7) starting from (+)-(1S)-menthyl-(R)-toluene-4-sulfinate, methylmagnesium bromide, methyl fluoroacetate, 4-pentenyl bromide and diazomethane is described. The absolute stereochemistry was unambiguously determined by X-ray analysis of (+)-(1S,2R,5S,RS)-5, an intermediate in the synthesis of the enantiomeric (+)-(1S,2R,5S)-2-fluoro frontalin (7).
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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    Paper (German National Licenses)
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