Synthesis of macrolide pheromones

This review considers pathways for the synthesis of macrocyclic lactones (macrolides) identified as components of pheromones of insects of the order Coleoptera (Cucujidae), genera Cryptolestes and Oryzaephilus —granary pests.Institute of Petrochemistry and Catalysis, Academy of Sciences of the Republic of Bashkortostan, Ufa. Institute of Organic Chemistry, Ufa Scientific Center, Russian Academy of Sciences, Ufa. Institute of Fine Organic Synthesis, Academy of Sciences of the Republic of Bashkortostan, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 526–548, July–August, 1995. Original article submitted July 15, 1994.     

10-Undecenoic acid in the synthesis of insect pheromones

The literature on the use of 10-undecenoic acid in the synthesis of insect pheromones is reviewed.Institute of Organic Chemistry, Ufa Scientific Center, Russian Academy of Sciences, 450054, Ufa, prospekt Oktyabrya 71, fax (3472) 35 60 66. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 87–96, March–April, 2000.     

Synthesis ofLepidoptera pheromones using acetylenes

Syntheses of acetogenin pheromones using acetylene derivatives are reviewed.Institute of Petroleum Chemistry and Catalysis, Academy of Sciences of the Republic of Bashkortostan and Ufa Scientific Center, Russian Academy of Sciences, 450075, Ufa, pr. Oktyabrya, 141. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 12–31, January–February, 2000.     

Insect pheromones and their analogs. LVIII. Synthesis of hexadeca-7Z,11E-dien-1-yl acetate — a component of the sex pheromones ofPectinophora gossypiella andSitotroga cerealella

A new synthesis of hexadeca-7Z,11E-dien-1-yl acetate — a component of the sex pheromones of the pink bollworm (Pectinophora gossypiella) and the Angoumois grain moth (Sitotroga cerealella) — is proposed that is based on a thermal Claisen rearrangement.Scientific-Research Institute of Small-Tonnage Chemical Products and Reagents, Ufa, fax 8-(3472) 43 17 31. Ufa State Petrotechnical University. Institute of Petrochemistry and Catalysis, Academy of Sciences of the Republic of Bashkortistan, Ufa, fax-8(3472) 31 27 50. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 231–234, March–April, 1998.     

Determination of fatty acid compositions by the direct transesterification of seed lipids

The possibility of using the direct alkaline transesterification of seed lipids for the express analysis of fatty acid compositions has been shown on 11 samples of plant seeds.Institute of Organic Chemistry, Ufa Scientific Center, Russian Academy of Sciences, Ufa, fax (3472) 35 60 66. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 172–175, March–April, 1998.     

Synthesis of methyl-branched low-molecularmass insect bioregulators from the products of the acid decyclization of 4-methyltetrahydropyran

This review generalizes work on the chemoselective synthesis of racemic methyl-branched insect pheromones and the juvenoid hydroprene from 1,5-bifunctional 3-methylpentanes produced by the acid opening of the ring of 4-methyltetrahydropyran.Institute of Organic Chemistry, Ufa Scientific Center, Russian Academy of Sciences. Scientific-Research Institute of Fine Organic Synthesis Academy of Sciences of the Republic of Bashkortostan, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 170–177, March–April, 1977.     

Autooxidation of 2-isobutyl-5,6-benzo-1,3,2-dioxaborepane

Using PMR, IR, and mass spectrometric methods it was shown that the main autooxidation product upon prolonged storage of 2-isobutyl-5,6-benzo-1,3,2-dioxaborepane is 2,2′-oxybis(5,6-benzo-1,3,2-doxaborepane). A. V. Bogatskii Physicochemical Institute, National Academy of Sciences of Ukraine, Odessa 270080. Organic Chemistry Institute, Ufa Science Center, Russian Academy of Sciences, Ufa 450054. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1418–1421, October, 1998.     

Synthesis and conformation of 2-silylethynyl-substituted 2,4,4,6-tetramethyl-1,3-dioxanes

Reaction of 2,4,4,6-tetramethyl-1,3-dioxanium perchlorate with lotsich reagents led to the synthesis of new silylethynyl-substituted 2,4,4,6-tetramethyl-1,3-dioxanes. According to the data of¹H and¹³C NMR and x-ray diffraction analysis, it was established that the 1,3-dioxane ring of the products obtained has the chair conformation.Kuban' State Technological University, Krasnodar 350072, Russia. Ufa State Oil Technical University, Ufa 450062, Russia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 487–493, April, 1998.     

Transformation of glycyrrhizic acid. VII. Synthesis of triterpene glycopeptides containing alkyl esters of L-amino acids

The synthesis has been effected by the activated N-hydroxy succinimide ester method of new triterpene glycopeptides derived from glycyrrhizic acid, containing fragments of alkyl (ethyl, propyl, butyl) esters of L-amino acids. Institute of Organic Chemistry, Ufa Scientific Center, Russian Academy of Sciences, 45005, Ufa, Prospekt Oktyabrya, 71. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 261–268, March–April, 1994.     

Transformation of glycyrrhizic acid. VII. Synthesis of triterpene glycopeptides containing alkyl esters of L-amino acids

The synthesis has been effected by the activated N-hydroxy succinimide ester method of new triterpene glycopeptides derived from glycyrrhizic acid, containing fragments of alkyl (ethyl, propyl, butyl) esters of L-amino acids.Institute of Organic Chemistry, Ufa Scientific Center, Russian Academy of Sciences, 45005, Ufa, Prospekt Oktyabrya, 71. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 261–268, March–April, 1994.     

Synthesis of dodeca-8e, 10e-dien-1-ol — the sex pheromone ofLaspeyresia pomonella via the acetolysis of 4-propenyl-1,3-dioxane

A new scheme has been developed for the synthesis of dodeca-8E,10E-dien-1-ol (the sex pheromone of the codling moth) from sorbyl acetate, available from 4-propenyl-1,3-dioxane through the intermediate diacetate of 3 propenyl-2-oxapentane-1, 5-diol.Scientific Research Institite of Fine Organic Synthesis, Academy of Sciences of the Republic of Bashkortostan, Ufa. Institute of Organic Chemistry of the Scientific Center, Russian Academy of Sciences, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp 602–604, July–August, 1996. Original article submitted January 29, 1996.     

Insect pheromones and their analogs LV. Synthesis of trideca-4E, 7Z-dien-1-YL acetate-component of the sex pheromone ofPhthorimaea opercucella

Starting from propargyl alcohol and using the thermal Claisen rearrangement at the stage of constructing the (E)-double bond, we have synthesized trideca-4E, 7Z-dien-1-yl acetate— a component of the sex pheromone of the potato mothPhthorimaea opercucella (Zeller).Scientific-Research Institute of Fine Organic Synthesis, Academy of Sciences of the Republic of Bashkortostan, Ufa. Ufa State University of Petroleum Technology. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 452–455, May–June, 1997.     

Synthesis from 10-undecenoic acid of octadeca-2E,13Z-dienylacetate, a component of the sex pheromones ofSynanthedon tipuliformis andZenzera pyrina

A new synthesis of octadeca-2E,13Z-dienylacetate from 10-undecenoic acid is developed by constructing the carbon framework of the pheromone in the key step and introducing the 2E double bond by Doebner condensation of hexadec-11-ynal and malonic acid.Institute of Organic Chemistry, Ufa Scientific Center, Russian Academy of Sciences, 450054, Ufa, prospekt Oktyabrya, 71, fax: (3472) 35 60 66. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 164–166, March–April, 2000.     

Structure of liquid water with ST2 model potentials in the temperature interval 273–373 K

Ufa Aviation Institute. Translated from Zhurnal Strukturnoi Khimii, Vol. 31, No. 4, pp. 69–73, July–August 1990.     

Dynamics of the alkaloid content of Lilium martagon

Institute of Chemistry of Plant Substances, Academy of Sciences of Uzbek SSR, Tashkent. South-Urals Reserve, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 4, p. 559, July–August, 1990.     

Radiothermoluminescence study of the degradation of the surface of superconducting SmBa2Cu3O6.9

Institute of Chemistry, Urals Branch, Russian Academy of Sciences, 450054 Ufa. Translated from Izvestiya Akademii Nauk, Seriya Khimicheskaya, No. 3, pp. 763–764, March, 1992.     

Infrared spectra and structure of solutions of lithium perchlorate and thiocyanate in ethylacetate-acetonitrile binary solvents

S. Ordzhonikidze Ufa Aviation Institute. Translated from Zhurnal Strukturnoi Khimii, Vol. 29, No. 4, pp. 75–79, July–August, 1988.     

Molecular-mass distribution of dissolved organic matter of water sources and drinking water of Ufa

Using the size-exclusion chromatography method, the molecular-mass distribution of dissolved organic matter of drinking water and water sources of Ufa is studied. The influence of seasonal changes and various water treatment stages on the molecular-mass distribution of dissolved organic matter is shown.     

Emission of Ph3C. in the autooxidation reactions of triphenylmethyllanthanide chlorides

Institute of Chemistry, Bashkir Science Center, Urals Branch, Russian Academy of Sciences, 450054 Ufa. Translated from Izvestiya Akademii Nauk, Seriya Khimicheskaya, No. 3, pp. 762–763, March, 1992.     

Preparation of 2,5-pentamethylene-4,4,5,-tetramethyloxazolidine by radical cycloalkylation of N-isopropylidenecyclohexylamine

Boshkir State Institute of Medicine, Ufa 450000. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 846–847, June, 1994. Original article submitted May 31, 1994