A series of 1-benzyl-3-hydroxy-1,2,3,6-tetrahydropyridines, multipurpose synthons for fine organic synthesis and potential antiviral compounds, was prepared by the rearrangement of a number of 1-benzyl-3,4epoxypiperidines under treatment with lithium amides. 3,4-Epoxypiperidines were obtained by oxidation of 1,2,5,6tetrahydropyridines trifluoroacetates with a trifluoroperacetic acid. Convenient synthetic routes were found and developed. A conformation analysis of the series of stable 3,4-epoxypiperidines and 3-hydroxy-1,2,3,6tetrahydropyridines was carried out.

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We report a new approach to preparing iminosugars -4-substituted 1-benzylpiperidin-3,5-diols by reaction of 1-benzyl-4,5-epoxypiperidine-3-ols in the presence of lithium perchlorate. This regio-and stereoselective synthesis proceeds via successive nucleophilic cleavage of 1-benzyl-4,5-epoxypiperidin-3-ols by benzylamine, thiophenol and diallylamine. Initial 1-benzyl-4,5-epoxypiperidin-3-ols were obtained by oxidation of trifluoroacetates of 1-benzyl-1,2,3,6-tetrahydropyridin-3-ols.

Pyridine derivatives R 0380Synthesis and Stereochemistry of 3-Hydroxy-1,2,3,6-tetrahydropyridines. -3-Hydroxy-1,2,3,6-tetrahydropyridines (III), (VI), and (VII) with potential antiviral activity are conveniently synthesized via oxidation of tetrahydropyridines (I) or (IV) with peroxytrifluoroacetic acid followed by rearrangement of the intermediate epoxides under the action of LDA. -(GRISHINA, G. V.; BORISENKO, A. A.; VESELOV, I. S.; PETRENKO, A. M.; Russ. J. Org. Chem. 41 (2005) 2, 272-278; Lomonosov Moscow State Univ., Moscow 119899, Russia; Eng.) -R. Staver 39-132