ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Racemic diaminosugars were easily obtained by a regio- and stereoselective three-step synthetis. In the first step, regiospecific hetero-Diels-Alder cycloadditions between 1,2-dihydropyridines 1a and 10 and nitrosobenzene led to the bicyclic compounds 2a and 11, respectively, cis-Glycol formation starting from these latter adducts, followed by hydrogenolysis of the N—O bond and by exhaustive acetylation of the OH-groups, led to the diaminolyxose 5, the diaminomannose 14 and the diaminoallose 15. When starting from benzyl 1,2-dihydropyridine-1-carboxylate (1b) and using the same reaction sequence, the racemic piperidine derivative 8 was obtained.
Additional Material:
4 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19850680112
