M. S. Yunusov

Selective Oxidation of Betulin by Cr(VI) Reagents

Oxidation of betulin by pyridinium dichromate, pyridinium chlorochromate, and K2Cr2O7 -H2SO4 in the presence of tetrabutylammonium bromide was studied. Products of regioselective C-3, C-28-, and exhaustive oxidation, 28-hydroxylup-20(29)-3-one, 3β-hydroxy- and 3-oxolup-20(29)-en-28-al were obtained.

Synthesis and stereochemistry of some 3-azabicyclo[3.3.1]nonane derivatives

Michael reactions of methyl (ethyl) 1-benzyl-4-oxopiperidine-3-carboxylates with a number of α,β-unsaturated carbonyl compounds result in formation of 6- and 6,8-substituted methyl (ethyl) 3-benzyl-9-oxo-3-azabicyclo[3.3.1]nonane-1-carboxylates. Stereochemical aspects of these reactions were studied, and some further transformations of the products were performed.

Oxidation of diterpenoid alkaloids with dimethyldioxirane

Oxidation of diterpene alkaloids by dimethyldioxirane was studied with eldeline, talatizamine, aconitine, and zongorine as examples. Nitrones and 19-oxo derivatives of bases were obtained. The results of the oxidation allow one to draw an analogy with the oxidation by KMnO4 and to suggest a mechanism of the reaction.

Fluorescence of the diterpenoid alkaloids lappaconitine andN-deacetyllappaconitine in acetonitrile

The absorption, excitation, and fluorescence spectra of the diterpenoid alkaloids, lappaconitine andN-deacetyllappaconitine, in acetonitrile were studied. On the basis of the coincidence of the spectra with the analogous spectra of model compounds, methyl esters of anthranilic andN-acetylanthranilic acids, the conclusion was drawn that the—OOC(Ph)NRH groups are fluorochromes in the alkaloids studied. The high quantum yield of fluorescence and the bathofluoric shift in the luminescence and absorption spectra ofN-deacetyllappaconitine were explained by an increase in the electron-releasing ability of the —NRH group in the deacetylation of lappaconitine.

“Anhydrolycaconitine”, a new diterpene alkaloid fromAconitum septentrionale K

A new alkaloid, anhydrolycaconitine (C36H46N2O9), was isolated from roots ofAconitum septentrionale K. Based on the results of1H and13C NMR and IR spectroscopy and mass spectrometry of the alkaloid and the product of its alkaline hydrolysis and on the data of X-ray diffraction analysis of the hydrolysis product, the structure of 1α, 6β, 14α, 16β-tetramethoxy-7-oxo-18-succinylanthranoyloxy-17-(7→8)abeo-aconane was assigned to anhydrolycaconitine.

Synthesis of Optically Active Methyl 12-Oxo-9,10-epoxyoctadecanoate

The procedure for synthesizing optically active methyl 12-oxo-9,10-epoxyoctadecanoate (enantio- meric purity ∼90%) was developed, starting from ricinolic acid methyl ester.

A new norditerpenoid alkaloid acsonine from the roots of Aconitum kusnezoffii Reichb.

The known norditerpenoid alkaloid mesaconitine and a new alkaloid acsonine 1 were isolated from the roots of Aconitum kusnezoffii Reichb. The structure of 1 was established based on spectroscopic data.

Lipids, lipophilic components, and biologically active fractions of Viburnum opulus L. seeds.

Methyl and triterpenyl fatty-acid esters and triterpenic acids are isolated and identified from seeds ofViburnum opulus(Caprifoliaceae). The biological activity of pigments and proteins is determined

Mass spectrometry in structural studies of diterpene alkaloids

Data on the use of electron impact mass spectrometry for the determination of the structures of diterpene alkaloids are surveyed and described systematically.

Synthesis and Antiarrhythmic Activity of 5-Amino-exo-3-azatricyclo[5.2.1.02,6]decan-4-one

Exo-2-amino-exo-3-aminomethylbicyclo[2.2.1]heptane (I) and 5-amino-exo-3-azatricyclo[5.2.1.02,6]decan-4-one (II) were synthesized and characterized with respect to antiarrhythmic activity. Compound II exhibited antiarrhythmic activity with ED50 = 0.28 and 0.33 mg/kg on the aconitine and calcium chloride models of arrhythmia, respectively. Compound I did not show antiarrhythmic activity and exhibited acute toxicity corresponding to LD50 = 450 mg/kg.