Synthesis of hexadec-9Z-enal — One of the components of the sex pheromone of Heliothis armigera

Hexadec-9Z-enal — a component of the sex pheromone of the cotton bollwormHeliothis armigera — has been obtained by a three-stage synthesis from 9-acetoxynonanal and n-heptyltriphenylphosphonium bromide followed by reduction and oxidation.A. S. Sadykov Institute of Bioorganic Chemistry, Uzbekistan Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 276–277, March–April, 1992.     

Pheromones of insects and their analogs. XXVIII. Practical synthesis of tetradeca-9Z,12E-dien-1-yl acetate — A component of the sex pheromones of insects of the order lepidoptera

Tetradeca-9Z,12E-dien-l-yl acetate, a sex pheromone of the Indian meal mothPlodia interpunctella has been synthesized from the readily available product of the hydrodimerization of butadiene — octa-1,7-diene.Institute of Chemistry, Bashkir Scientific Center, Urals Branch, Academy of Sciences of the USSR, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 276–279, March–April, 1991.     

Synthesis of (E)-dodec-3-en-1-yl acetate — The main component of sex pheromones of Scrobipalpa ocellatella and Scrobipalpopsis solanivora

(E)-Dodec-3-en-l-yl acetate — the main component of the sex pheromones ofScrobipalpa ocellatella andScrobipalpopsis solanivora — has been obtained by a three-stage synthesis from decanal and malonic acid. The overall yield of pheromone was 33% calculated on the initial aldehyde.A. S. Sadykov Institute of Bioorganic Chemistry, Uzbek SSR Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 682–683, September–October, 1988.     

Isolation and identification of a supplementary component of the sex pheromone of Mamestra brassicae females

Using gas-liquid chromatography and mass spectrometry, from an extract of the sex pheromone of females of the cabbage mothMamestra brassicae L. an additional component of the pheromone has been isolated and identified — heptadeccis-11-en-1-ol acetate.All-Union Scientific-Research Institute of Biological Methods of Plant Protection, Kishenev. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 235–238, March–April, 1986.     

Pheromones of insects and their analogs

From cyclohexene and caproaldehyde, using ozonolysis and the Knoevenagel reaction, we have synthesized hexadeca-7Z,11E-dien-l-yl acetate — the sex pheromone ofSitotroga cerealella and a component of the sex pheromone ofPectinophora gossypiella.Institute of Chemistry, Bashkir Scientific Center, Urals Branch, Russian Academy of Sciences, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 704–707, September–October, 1991.     

Coleopteran pheromones. Communication 9. Synthesis of the attractant of the leaf beetle diabrotica virgifera virgifera (coleoptera: Chrysamelidae) from (+)-3,7-di-methyl-1,6-octadiene

Conclusions Simple routes for the synthesis of (2RS, 8R)-(–)-2-propionoxy-8-methyldecane (I) the pheromone of the leaf beetleDiabrotica virgifera virgifera — from chiral monofunctional synthons, obtained from the available (S)-(+)-3,7-dimethyl-1,6-octadiene, were developed.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2080–2083, September, 1987.It corresponds to Communication 4 in the series Terpenes in Organic Synthesis. For the preceding Communication, cf. [1].     

Synthesis of dodec-5E-en-1-ol — The pheromone of Tricimba cincta — And tetradec-5E-1-yl acetate — An imitator of the pheromone of Rhynchopacha sp.

On the basis of a modified Knoevenagel reaction starting from octanol and decanal, the stereodirected synthesis has been effected of dodec-5E-en-ol (the pheromone of the grass flyTricimba cincta — and tetradec-5E-en-yl acetate) an imitator of the pheromone of the mothRhynchopacha sp. A. S. Sadykov Institute of Bioorganic Chemistry, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 129–132, January–February, 1991.     

Insect pheromones and their analogues

A scheme has been developed for the synthesis of (R)-(–)-10-methyltridecan-2-one, the sex pheromone of the southern corn rootworm (Diabrotica undecimpunctata) using as the chiral synthon (R)-(+)-methylheptenal obtained by the hydroperoxide oxidation of the readily available (S)-(+)-dihydromyrcene.Institute of Chemistry, Bashkir Scientific Center, Urals Branch, Russian Academy of Sciences, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 125–129, January–February, 1992.     

Glycals in stereochemical synthesis

Enantiomerically pure (14R)-14-methylhexadeca-8Z-enal (cis-trogodermal) — the aggregation pheromone of the khapra beetle (Trogoderma) — and its (14S,8Z)-enantiomer has been effected from di-O-benzoyl-D- and -L-arabinals.Institute of Chemistry, Bashkir Branch, Urals Branch, Russian Academy of Sciences, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 707–712, September–October, 1991.     

Insect pheromones and their analogs. XLVII. Synthesis of 11-oxododeca-3,6-diynoic acid — The acyclic precursor of a macrolide component of pheromones of Oryzaephilus mercator and O. Surinamensis

A new approach is proposed to the synthesis of 11-oxododeca-3,6-diynoic acid — the acyclic precursor of a macrolide component of pheromones ofOryzaephilus mercator andO. surinamensis — from the readily available tetrahydropyran or allylacetone via the intermediate 5-bromo-2,2-ethylenedioxypentane.Institute of Organic Chemistry, Urals Division, Russian Academy of Sciences, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 288–292, March–April, 1993.     

Sesquiterpene lactones from Inula japonica

Summary 1. FromInula japonica a new sesquiterpene lactone — deacetylinulicin — has been isolated.2. Spatial formulas have been put forward for inulicin and deacetylinulicin (Ia and Ib, respectively).All-Union Scientific-Research Institute of Medicinal Plants. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 730–733, November–December, 1974.     

Insect pheromones and their analogues. XLVI. Synthesis of 13RS-hydrooxytetradec-5Z-enoic acid — The acyclic precursor of the macrolide component of the pheromone of Cryptolestes pusillus

New routes for the synthesis of 13RS-hydroxytetradec-5Z-enoic acid — the acyclic precursor of the macrolide component of the pheromone ofCryptolestes pusillus have been developed on the basis of the readily accessible 1-methylcycloocta-1Z, 5Z-diene or isopropyl nona-3E,8-dienoate.Institute of Biological Plant Protection, Moldovian Academy of Sciences, Kishinev. Scientific-Research Institute of Forestry and Forestry Mechanization, Pushkino. Moscow Institute of Wood Technology; and Georgia Institute of Mountain Forestry, Tbilisi. Translated from Khimiya Prirodnykh Soedeninii, No. 1, pp. 150–155, January–February, 1993.     

The seed oils of some species of the family Cruciferae

Summary The physicochemical properties of the oils of the seeds of seven plants of the family Cruciferae —Cakile maritima, Sisymbrium altissimum, Sisymbrium Loeselii, Descurainia Sophia, Erysimum cheiranthoides, Brassica amoracioides andCrambe pontica — have been studied and their fatty acid compositions have been determined. The results obtained showed no marked differences from those given in the literature.Zaporozhe Medical Institute. Ukrainian Scientific-Research Institute of the Oils and Fats Industry. Zaporozhe Oils and Fats Combine. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 15–18, January–February, 1973.     

Synthesis of 6E-Nonen-1-OL from butadiene-phenol telomer

Conclusions 6E-Nonen-1-ol, theCeratitis capitata pheromone, was synthesized from the telomer of butadiene with phenol.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1181–1182, May, 1982.     

Structure of artabin

Summary FromArtemisia absinthium L. a new sesquiterpene lactone of the germacrane type — artabin — has been isolated. Structure I is proposed for it.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR. Translated from Khimiya Prirodnykh Soedineii, No. 6, pp. 691–694, November–December, 1970.