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  • Alkaloids  (1)
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  • 1
    ISSN: 1434-193X
    Keywords: Alkaloids ; Alkylations ; Asymmetric synthesis ; Grignard reactions ; Nitrogen heterocycles ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---Treatment of salts 1a-b with Grignard reagents gives, after reduction of the resulting unstable dihydropyridines 7, the tetrahydropyridines 8a-c, with modest selectivities but in very few steps and under practical conditions. Higher stereo- and regioselectivities are obtained with salt 1c which gives the tetrahydropyridines 15a-e. In addition, the dihydropyridine intermediates 11b cyclize to give the new oxazolidine derivatives 12a-e, which turn out to be good precursors of the 2,6-trans-disubstituted tetrahydropyridines 21a-e. Selective syntheses of (-)-lupetidin, (+)-solenopsin, and indolizidines (-)-5 and (-)-6 are presented as representative examples of applications.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
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