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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