Synthesis of modified hexaprenol WC5OH from glutaraldehyde derivatives

A new procedure was developed for building linear Z-isoprenoids from glutaraldehyde derivatives as nonisoprenoid precursors, and is illustrated by the synthesis of hexaprenol WC₅OH.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 89–97, January, 1990.     

Stereospecific synthesis of octaprenols WT3C4OH and WT3C3TOH

A total synthesis of the above prenols has been carried out.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2333–2338, October, 1991.     

Synthesis of dolichol-type (S)-hexa- and (S)-heptaprenols

(R)-1-Phenysulfonyl-2-methylbutan-4-ol has been used as starting material for the stepwise synthesis of the dolichol-related hexa- and heptaprenols (S)-3,7, 11,15,19,23-hexamethyltetraeicosa-6Z,10Z,14E,18E,22-pentaene-1-ol and (S)-3,7, 11,15,19,23,27-heptamethyloctaeicosa-6Z,10Z,14E,18E,22E,26-hexaen-1-ol.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2052–2056, September, 1989.     

Reaction of 4-methyl-5,6-dihydro-2h- and 4-methylenetetrahydropyrans with phenylsulfinyl chloride

4-Methyl-5,6-dihydro-2H- and 4-methylenetetrahydropyrans undergo an ene- type reaction with phenylsulfinyl chloride in the presence of ZnCl₂ to give the corresponding allylic sulfoxides.October Revolution Fortieth Anniversary, Bashkir State University, UfaTranslated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1446–1447, June, 1990.     

Synthesis of shikalkin and certain related compounds

A successful total synthesis of a biologically active pigment from plants of the Boraginaceae family was carried out with naphthazarine as the starting material, and using the 1,4,5,8-tetramethoxynaphthalene, the corresponding 2-vinyl derivative and its epoxide or a cyclopropane adduct with diazoacetic ester at the key stages. In the course of developing the scheme of the synthesis of shikalkin, its three analogs were obtained, differing in the nature of the monoterpenoid side chain.For preliminary report, see [1].Pacific Ocean Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, 690022 Vladivostok. N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, 117913 Moscow. Translated from Izvestiya Akademii Nauk, Seriya Khimicheskaya, No. 8, pp. 1901–1910, August, 1992.     

Transformed steroids

Conclusions The enamination of the 21-hydroxymethylene derivative of the 16,17-dehydropregnenolone under conventional conditions is accompanied by the C-alkylation of the intermediate enamino ketone by a second molecule of the starting -keto aldehyde.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 431–434, February, 1974.     

Some properties of the adduct of benzenesulfinyl chloride with myrcene

Conclusion The reaction of PhSOCl with myrcene at high pressure leads to the cis-1,4 addition product.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5 pp. 1143–1145, May, 1987.