A simple synthesis of (±)-2,6-dimethylocta-5(<Emphasis Type="Italic">Z</Emphasis>),7-diene-4-ol and its attractant activity for the bark beetle <Emphasis Type="Italic">Ips typographus</Emphasis>

A simple method for the synthesis of (±)-2,6-dimethylocta-5(Z),7-diene-4-ol possessing a high pheromone activity for the bark beetle Ips typographus was developed.__________Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2245–2247, October, 2004.     

New versions of Pd0-catalyzed allylation of C-nucleophiles

New “one-pot” protocols proposed for Pd⁰-catalyzed allylation of C-nucleophiles involve deprotonation of the corresponding CH acids with in situ generated dialkylamide and alkoxide anions. Dedicated to Academician O. M. Nefedov on the occasion of his 75th birthday. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2024–2026, November, 2006.     

Stereocontrolled synthesis of (+)- and (−)-iridomyrmecin from citronellene enantiomers

Natural (+)-iridomyrmecin and its unnatural enantiomer (−)-iridomyrmecin were synthesized by intramolecular [3+2] dipolar cycloaddition of silyl nitronates that had been generated from the nitro derivatives of (+)- and (−)-citronellenes, respectively. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1683–1687, September, 1997.     

The reactivity of N,N-dialkyl-N-(3-phenylsulfinyltetrahydrofuran-2-ylidene)ammonium bromide

trans-Stereoselective electrophilic cyclization of (2R*,SS*)-N, N-diisopropyl-2-phenylsulfinylpent-4-enamide under the action of bromine afforded (3R*,5S*, SS*)-N-(5-bromomethyl-3-phenylsulfinyltetrahydrofuran-2-ylidene)-N,N-diisopropylammonium bromide. Its transformations under the conditions of hydrolysis, dehydrobromination, and hydride reduction were studied. Dedicated to Academician V. A. Tartakovsky on the occasion of his 75th birthday. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1485–1490, August, 2007.     

Computer-aided design and discovery of protein–protein interaction inhibitors as agents for anti-HIV therapy

Protein–protein interactions (PPI) are involved in most of the essential processes that occur in organisms. In recent years, PPI have become the object of increasing attention in drug discovery, particularly for anti-HIV drugs. Although the use of combinations of existing drugs, termed highly active antiretroviral therapy (HAART), has revolutionized the treatment of HIV/AIDS, problems with these agents, such as the rapid emergence of drug-resistant HIV-1 mutants and serious adverse effects, have highlighted the need for further discovery of new drugs and new targets. Numerous investigations have shown that PPI play a key role in the virus’s life cycle and that blocking or modulating them has a significant therapeutic potential. Here we summarize the recent progress in computer-aided design of PPI inhibitors, mainly focusing on the selection of the drug targets (HIV enzymes and virus entry machinery) and the utilization of peptides and small molecules to prevent a variety of protein–protein interactions (viral–viral or viral–host) that play a vital role in the progression of HIV infection.     

NorTRACK product tracking system—development and implementation

This paper presents the experience gained by developers and users with implementation and operation of NorTRACK^TM, a real-time computerized product tracking system. A Programmable Logic Controller (PLC) collects and transfers data in real time to NorTRACK’s Oracle^TM database on a Windows NT^TM server network. After extensive development and Beta testing at MDS Nordion’s Canadian Irradiation Centre in Montreal, Canada, NorTRACK was installed in January 1997 with a new irradiation facility in Ethicon Endo-Surgery Inc.’s Albuquerque plant in the United States. NorTRACK communicates with the irradiator control and safety system, the plant's central manufacturing database, an innovative pallet staging and tote loading robot, and an automated dosimetry reading system. This integrated system allows the sterilization facility to monitor the irradiator operation and the flow of many products, through varied processing modes, continuously and reliably. As a result of operating with NorTRACK, both MDS Nordion’s CIC facility and the Endo-Surgery manufacturing site, are beginning to realize unique benefits in their respective operations. MDS Nordion is also initiating several future product enhancements and additional productivity modules. This paper describes the NorTRACK system, the various stages of the development project and Beta tests, and the experience of the users to date in their operations.     

An undecaprenyl phosphate analog containing the phenoxy group at the ω-end of the oligoisoprene chain

A simple method for the preparation of a biologically active analog of bacterial undecaprenyl phosphate bearing the phenoxy group at the ω-end of the chain was developed on the basis of accessible polyprenols from mulberry (Morus nigra) leaves. It includes the selective van Tamelen epoxidation of the ω-terminal isoprene unit of polyprenyl acetates, conversion of the epoxides into ω-terminal aldehydes, their hydride reduction into hydroxy acetates followed by the Mitsunobu condensation with phenol, and phosphorylation of the resulting phenoxy alcohols. The biological activity of the obtained phosphates was tested by the radiometry method in the initiation of O-antigenic polysaccharide assembly reaction using the cell membrane preparations from the Gram-negative bacteria Salmonella arizona O:59 and Aeromonas hydrophila AH-1.     

A simple method for preparing racemic dolichols from the polyprenols of pine needles (Pinus silvestris)

A simple method for preparing racemic mammalian dolichols by a three-stage transformation of a native mixture of plant polyprenols has been developed. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1009–1011, May, 1999.     

Synthesis of polyprenylamines from plant polyprenols

A simple method for the synthesis of polyprenylamines by a two-step transformation of plant polyprenol mixtures has been developed.     

Stereoselective synthesis of 2,4-disubstituted butanolides

A series of 2,4-disubstituted butanolides was prepared based on the trans-stereoselective electrophilic cyclization of substituted N-(pent-4-enoyl)pyrrolidines. The butanolides may be considered as synthons for this type of natural products. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 124–129, January, 2007.