Method for mild trimethylsilylation of the 14α-hydroxy group in ecdysteroids

In the reactions of poststerone derivatives and 20-hydroxyecdysone with (trifluoromethyl)trimethylsilane catalyzed by tetrabutylammonium fluoride, the 14-hydroxy group is readily subjected to trimethylsilylation.     

Identification and biological activity of the volatile organic substances emitted by plants and insects II. Sesquiterpene composition of the native scent of leaves of the potatoSolanum tuberosum

By dynamic gas extraction of the volatile components of the native scent of the leaves of the potatoSolanum tuberosum L. growing under natural conditions, followed by the gas-chromatographic separation and massspectrometric analysis of the substances obtained, the following sesquiterpene compounds have been identified:trans-andcis-caryophyllenes, -ylangene, -copaene, -bourbonene, -elemene, Z--farnesene, aromadendrene, -humulene, -elemene, -bisabolene, -cadinene, and -cadinene.Institute of Petrochemistry and Catalysis, Academy of Sciences of the Republic of Bashkortostan, and Ufa Scientific Center, Russian Academy of Sciences. Ufa-450075, Prospekt Oktyabrya, 141, tel./fax 7+(3472) 312750; ink@anrb.ru. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 472–477, July–August, 1999.     

Pheromones of insects and their analogs LIV. Synthesis of dodec-9E-en-1-ol and its acetate —components of the sex pheromone ofSparganothis pilleriana

Using the Claisen rearrangement in the construction of a double bond with the E configuration, we have synthesized dodec-9E-en-l-ol and its acetate, which are components of the sex pheromone ofSparganothis pilleriana.Scientific Research Institute of Fine Organic Synthesis of the Academy of Sciences, Republic of Belarus. Ufa State Petroleum Technical University. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 936–939, November–December, 1996. Original article submitted May 11, 1996.     

Insect pheromones and their analogs. XII. Synthesis of the isomeric dec-5-enyl acetates — The sex pheromones ofAnarsia lineatella andAgrotis segetum

A new route for the synthesis of dec-5E- and -5Z-enyl acetates — the sex pheromones of the peach-tree borer and of the turnip moth — is proposed which is based on the two-stage hydroxyethylation of hex-1-yne using 2-chloroethyl vinyl ethers and ethylene oxide.Institute of Chemistry, Bashkir Branch, Academy of Sciences of the USSR, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 395–398, May–June, 1985.     

Synthesis of the cyclic isomer of the vitamin K1 dihydro derivative (naphthotocopherol) and its analogs with the shortened and ω-functionalized side chain

(2RS,4′ RS,8′ RS)-Naphthotocopherol and its optically active short-chain analog were synthesized by the condensation of menadiol acetate with (3 RS,7 RS,11 RS)-isophytol and (3 RS,4 S)-3,4,8-trimethylnon-1-en-3-ol (ee ∼50%) in the presence of aluminosilicate Zeocar-10. Using (+)-camphor-10-sulfonic acid as a catalyst, naphthotocopherol analogs with the unsaturated isoprenoid side chain were obtained from (3 RS)-linalool or (3 RS,4 S)-3,4,8-trimethylnona-1,7-dien-3-ol. Ozonolysis of these compounds produced the corresponding ω-formyl derivatives. Dedicated to Corresponding Member of the Russian Academy of Sciences E. P. Serebryakov on the occasion of his 70th birthday. __________ Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 952–957, April, 2005.     

Insect pheromones and their analogues XXV. Synthesis of acetylenic precursors of pheromones from undecylenic acid

The selective ozonolysis of pentadec-1-en-12-yne and heptadec-1-en-12-yne, synthesized from the readily available undecylenic acid, has given tetradec- and hexadec-11-yn-1-ols — acetylenic precursors of a number of pheromones of insects of the order Lepidoptera. Institute of Chemistry, Bashkir Scientific Center, Urals Branch, Academy of Sciences of the USSR, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 823–825, November–December, 1990.     

Synthesis of triterpene acids conjugates with α-tocopherol synthetic analogs

Heterodimers were synthesized of pharmacologically important α-tocopherol synthetic analogs with triterpene acids(betulonic, betulinic), potential polyfunctionsl drugs possessing antioxidant activity. The combination of the fragments of biologically active substances was performed through linkers (residues of succinic acid, hydrazine, glycine, tetramethylenediamine) binding the side chain of the antioxidant molecule with atoms C³ or C²⁸ of the terpenoid.