E. V. Salimova

Insect pheromones and their analogs LIX. A new method for the synthesis of components of the sex pheromones of insects of the genusMalacosoma

A new method has been developed for the synthesis of the main components of the sex pheromones of insects of theMalacasoma genus that is based on the selective transformation of the product of the partial ozonolysis of cyclohexa-1,4-diene — methyl 6-oxohex-4E-enoate.

Synthesis and modifications of alkyne derivatives of dihydroquinopimaric, maleopimaric, and fumaropimaric acids

Reactions of maleopimaric and dihydroquinopimaric acid chlorides with propargyl alcohol and propargylamine afforded new terminal diterpene alkynes, and Sonogashira cross-coupling of the latter with 4-iodonitrobenzene led to the formation of arylalkynyl derivatives of Diels–Alder adducts of levopimaric acid.

Oxidative transformations of polyprenols

Oxidative transformationsinvolving the hydroxylsand ω-methylsof polyprenolsisolated from birch greenery (7-9 isoprene units in the chain) were used to produce α,ω-diols, diesters, aldehydoalcohols, and hydroxyacids. The products are of interest as potential anti-inflammatory, antiulcer, hepatoprotective, and cardio-active preparations.

Synthesis and antimicrobial activity of quinopimaric and maleopimaric acids

A number of nitrogen-, bromine-, and sulfur-containing derivatives of diene adducts of levopimaric acid have been synthesized. The testing of the compounds on Staphylococcus aureus and Klebsiella pneumoniae bacteria has shown that the compounds possess a weak antimicrobial activity.

Ozonation of Quinopimaric Acid Methyl Ester and Its 2,3-Dihydro Derivatives with Sterically Hindered Double Bonds

Ozonation of quinopimaric acid methyl ester and its 2,3-dihydro derivatives involves 1,2-addition of ozone to the sterically hindered double bonds with formation of peroxy epoxides and intramolecular interaction products.

Synthesis of aryl-containing isoprenoids from 1,5-dimethylcycloocta-1,5-diene

A procedure has been developed for the synthesis of Pro-Drone homo analogs from the ozonolysis products of 1,5-dimethylcycloocta-1,5-diene and 1,5-dimethylcyclooctene.

Convenient one-pot synthesis of resin acid Mannich bases as novel anticancer and antifungal agents

AbstractThe one-pot three-component CuCl-catalyzed aminomethylation of the abietane diterpenoid propargyl esters by formaldehyde and secondary amines was studied for the first time. The novel diethylamino, pyrrolidine, and morpholine-substituted butynyl derivatives of abietic, dehydroabietic, levopimaric, maleopimaric and dihydroquinopimaric acids were obtained. It was shown that synthesis of the abietic acid propargyl ester by the reaction of the abietane diterpenoid with oxalyl chloride and dimethylformamide is accompanied by the formylation of the ring B at the C-7 position and the dehydrogenation of the ring C to form the dehydroabietic acid ester. The cytotoxic, antibacterial and fungicidal activities of the synthesized compounds were studied in vitro. The experimental results showed that the most promising compound was 7-formyl abietic derivative Mannich base with a pyrrolidine substituent, with an MIC of 16 μg/ml against methicillin-resistant S. aureus ATCC 43300, and 8 μg/ml against C. albicans ATCC 90028 and 4 μg/ml against C. neoformans H99; ATCC 208821. The dihydroquinopimaric acid derivative with the diethylamine fragment showed the greatest antiproliferative activity towards twelve tumor cell lines.

One-pot synthesis of 1,2,3-triazole derivatives of maleopimaric and dihydroquinopimaric acids

Effective one-pot synthesis of 1,2,3-triazole derivatives of maleopimaric and dihydroquinopimaric acids consists in the reaction of diterpene propargyl esters with organic azides generated in situ in the presence of СuI catalyst.

Ozonolysis of verbenone in methanol

The conditions of ozonolysis of verbenone in methanol strongly affect the mechanism of formation of the major product, (1R,3S)-3-acetyl-2,2-dimethylcyclobutane-1-carboxylic acid.

Decomposition of ozonolysis peroxide products of (+)-α- and (+)-β-pinenes in methanol by Fe(III) salts

The reaction of ozonolysis peroxide products of (+)-α and (+)-β-pinenes with Fe(III) salts in MeOH was studied. It was found that decomposition of methoxyhydroperoxides obtained via ozonolysis of (+)-β-pinene using FeCl3⋅6H2O occurred at room temperature with formation of nopinone and its 3-chloro derivative; under reflux, nopinone and p-isopropylphenol. Replacing FeCl3⋅6H2O by Fe(NO3)3⋅9H2O produced the single product nopinone. Decomposition of peroxide compounds obtained via ozonolysis of (+)-α-pinene using FeCl3⋅6H2O gave a mixture of (1S,3S)-3-acetyl-2,2-dimethyl-1-(2,2-dimethoxyethyl)cyclobutane and [(1S,3S)-3-acetyl-2,2-dimethylcyclobutyl]acetate.