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.     

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.     

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.     

Synthesis of racemic 8-nonene-2,4-diol, acyclic precursor of 1,3-dimethyl-1,9-dioxabicyclo[3.1.1]nonane

A new way of synthesis was developed for racemic 8-nonene-2,4-diol, the acyclic precursor of l.3-dimethyl-l,9-dioxabicyclo[3.l.l] nonane. The latter substance was isolated from the bark of an ordinary spruce affected with a pest Trypodendron Lineatum Oliv.     

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.     

Insect Pheromones and Their Analogs. LXI. Synthesis of 4E,10Z-Tetradecadien-1-ylacetate, a Component of the Lithocolettis ringoniella Sex Pheromone

A new scheme for synthesizing 4E,10Z-tetradecadien-1-ylacetate, the principal component of the apple leaf miner(Lithocolettis ringoniella)sex pheromone, is developed using a highly stereoselective Claisen rearrangement     

Synthesis of 4<Emphasis Type="Italic">E</Emphasis>,7<Emphasis Type="Italic">Z</Emphasis>-tridecadien-1-ylacetate,a component of the <Emphasis Type="Italic">Phthorimaea opercucella</Emphasis> sex pheromone

A new synthetic approach to 4E,7Z-tridecadien-1-ylacetate, a component of the Phthorimaea opercucella (Zeller) potato moth sex pheromone, was developed using a highly stereoselective Claisen rearrangement and Wittig reaction. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 235–236, May–June, 2007.     

Insect pheromones and their analogues XL. Synthesis of dodec-3Z-EN-11RS-olide (ferrulactone II — A racemic analogue of a component of the aggregation pheromone of Cryptolestes ferrugineus

A new route, based on the partial ozonolysis of -acetyl derivatives of alk-1-en-4-ynes, is proposed for the synthesis of 11RS-hydroxydodec-3Z-enoic acid, the cyclization of which gives dodec-3Z-en-11RS-olide (ferrulactone II) — a racemic analogue of one of the macrolide components of the aggregation pheromone of the rust-red grain beetle.Institute of Organic Chemistry, Urals Branch, Russian Academy of Science,s Ufa. Translated from Khimiya Prirodnykh Soedinenii, Nos. 3,4, pp. 423–429, May–August, 1992.     

Insect pheromones and their analogs. XLIX. Synthesis of tridec-4-en-1-yl acetate — The sex pheromone ofKeiferia lycopersicella

Using the Claisen rearrangement at the stage of constructing the double bond, we have synthesized tridec-4Een-1 yl acetate, the sex pheromone of the tomato pinwormKeiferia lycopersicella.Institute of Petrochemistry and Catalysis, Academy of Sciences of the Republic of Bashkortostan, Republic of Bashkortostan; b) Scientific-Research Institute of Fine Organic Synthesis, Academy of Sciences of the Republic of Bashkortostan. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 490–493, May–June, 1995. Original article submitted November 9, 1994.     

Synthesis of 5<Emphasis Type="Italic">Z</Emphasis>,9<Emphasis Type="Italic">E</Emphasis>-tridecadien-1-ylacetate,an attractant of <Emphasis Type="Italic">Trichoplusia ni</Emphasis>

A new synthetic scheme for 5Z,9E-tridecadien-1-ylacetate, an attractant of the cabbage looper Trichoplusia ni (Huebner) was developed using a highly stereoselective Claisen rearrangement.