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  • 2000-2004  (1)
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    ISSN: 1434-193X
    Keywords: Isotopic labeling ; Isotopic labeling ; Isotopic labeling ; Deuterium ; Carbon-13 ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---Three selectively labeled propynes were prepared either with deuterium or carbon-13 at position 3 and doubly labeled with carbon-13 at positions 1 and 2 by an alkylation reaction from the corresponding labeled or unlabeled monolithio acetylides and dimethylsulfates. Their lithiation with nBuLi gave the corresponding propynyllithium derivatives which reacted with dimethyl squarate to afford the corresponding propargylic alcohols. These were thermolysed in p-xylene to furnish [5-D3-methyl]-, [5-13C-methyl]-, and [5,6-13C2-2,5-cyclohexadienyl]ubiquinone. The farnesyl side chain was introduced onto the labeled quinones with farnesyl trimethyltin under BF3 catalysis to provide [5-D3-methyl]-, [5-13C-methyl]-, and [5,6-13C2-2,5-cyclohexadienyl]ubiquinone 3 (6c, 6b, 6a, respectively).
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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