New 2- and 3-methoxyquinopimaric-acid derivatives were synthesized by a Diels–Alder reaction of levopimaric acid and 2-methoxy-1,4-benzoquinone. The reaction rate and regioselectivity of the cycloaddition were increased significantly by using a Bmim·BF4 catalyst. Photolysis of 3-methoxyquinopimaric acid produced new scaffold derivatives. The compounds were characterized by NMR spectroscopy and elemental analysis.

A new synthetic method for 16-sulfanyl-15-oxa scaffold derivatives of quinopimaric acid was developed. The structures of all synthesized compounds were elucidated using NMR spectroscopy and elemental analysis.

New conjugates of the quinolizidine alkaloids (–)-cytisine and thermopsin were synthesized by alkylating their 9-amino derivatives with 1,3-dimethyl-5-formyluracil. The cytotoxic properties of the synthesized conjugates against cell lines HEK293, HepG2, and Jurkat were studied. Screening identified the lead compound 5-{[(3-benzyl-8-oxo-1,3,4,5,6,8-hexahydro-2H-1,5-methanopyrido[1,2-a][1,5]diazocin-9-yl)amino]methyl}-1,3-dimethylpyrimidine-2,4-(1H,3H)-dione, which suppressed metabolic activity of lymphoblastic leukemia cells with inhibitory concentration (IC50) 20.6 ± 2.1 μM (IC50 of reference compound 5-fluorouracil was 18.5 ± 3.3 μM).

Diels-Alder adducts of levoglucosenone with 1,3-butadiene, piperylene, and isoprene, and also some of their derivatives undergo allylic oxidation with CrО3·2Py only in the case when the effect of a keto group or of another electron-acceptor group in the γ-position with respect to the double bond is removed.

The antihypoxic activity of a series of quinopimaric acid scaffold derivatives was studied. It was shown that compounds 3 , 5 , and 8 increased the lifespan of mice in various hypoxia models.

The composition and seasonal dynamics of alkaloids of the aerial part of the Chamaecytisus ruthenicus (in the buds, flowers, leaves and branches on the budding, flowering and bearing periods) growing in the mountain-forest region of the Southern Urals mountains were investigated by GC/MS. It was investigated that the content of alkaloids of aerial part of this plant is maximal on the budding period, and it decreases by the bearing phase. Thus at all phases of seasonal development the content of alkaloids in branches considerably exceeds their content in the other parts of this plant. The eight alkaloids, including seven quinolizidine alkaloids – sparteine, 17-oxosparteine, d-lupanin, a -isolupanin, 17-oxolupanin, sophocarpine, 12- N -methylcytisine and the pyridine alkaloid – ammodendrine, were isolated and identified. The major components of total alkaloids of Ch. ruthenicus on the budding period are sparteine and d-lupanin; the total alkaloids decreases during seasonal development mainly at the expense of content reduction (up to disappearance) of sparteine. These data allow to draw a conclusion, that Ch. Ruthenicus can be an available and renewable source of the two mentioned quinolizidine alkaloids – sparteine and d-lupanin.

Epoxidation of diastereoisomeric benzyloxy derivatives of the levoglucosenone adduct with cyclopentadiene by treatment with m -chloroperoxybenzoic acid afforded a mixture of 1,2- and 1,4-epoxy derivatives. Intramolecular cyclization of the hydroxy derivatives of the same adduct by the action of I 2 -NaHCO 3 -MeCN gave products resulting from cleavage of the 1,6-anhydro bridge, reduction of the acetal moiety, and olefinaldehyde cyclization.

Sulfur-containing quinopimaric acid scaffold derivatives were synthesized. The structures of all synthesized compounds were proved using NMR spectroscopy and elemental analysis.

6-Chloro-, 6-chloroacetoxy-, and 16-(2-bromoacetyl)framework derivatives were synthesized from a photoadduct of quinopimaric acid.

A method for preparing optically active diterpene compounds of the aza-birdcage type that was based on reaction of oxa-scaffold derivatives of quinopimaric acid with primary amines, amides, and carbamides was developed.

Optically active amides, ureas, and thioureas were synthesized from cage acid chloride derived from quinopimaric acid.

Dimeric compounds formed as a result of thermal oligomerization of methyl 4-(1,3-dioxo-2,3- dihydro-1H-isoindol-2-yl)buta-2,3-dienoate were identified.

New nitrogen-containing and hydroxy derivatives of quinopimaric acid were synthesized, and their structure was determined by 1 H and 13 C NMR spectroscopy.

3 H -Pyrrolo[2,1- a ]isoindole-2,5-diones and isoindolo[2,1- a ]quinoline-5,11-diones were synthesized by intramolecular cyclization of N -[2-oxo-3-(triphenyl-λ 5 -phosphanylidene)propyl]- and N -[2-(triphenyl-λ 5 -phosphanylidene)acetyl]phthalimides, respectively, in the presence of ionic liquid ([bmim][BF 4 ], 10 mol %) as catalyst or under microwave irradiation.

Sulfur-containing heterocyclic compounds, oxo-tetrahydrothiophene and 1,2-dithian-4-one derivatives were synthesized from sulfonium ylides obtained on the basis of N,N–diphthalylcystine.

Photolysis was inverstigated of quinopimaric acid derivatives under various conditions. The structure of the photolysis products was proved with 1 H, 13 C, and mass spectra and XRD analysis.