(R)-4-Menthenone in the synthesis of optically pure sex pheromone of the peach leafminer moth (Lyonetia clerkella)

The synthesis of (14S)-methyloctadec-1-ene, sex pheromone of the peach leafminer moth (Lyonetia clerkella), is described to demonstrate a new potential of the synthetic use of (R)-4-menthenone.     

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.     

Ozonolytic Decyclization of (R)-4-Menthen-3-one

Ozonolytic decyclization of (R)-4-menthen-3-one is accompanied by fragmentation of the isobutyl group, leading to -functionalized 3-methylpentanoic acid derivatives.     

Insect pheromones and their analogues XLIII. Chiral pheromones from (S)-(+)-3,7-dimethylocta-1,6-diene 3. Synthesis of (4R)-4-methylnonan-1-OL — Sex pheromone of Tenebrio molitor and its racemic analogue

Starting from the readily available enantiomerically enriched (S)-(+)-3,7-dimethylocta-1,6-diene (ee ≃ 50%), we have synthesized (4R)-4-methylnonan-1-ol — the sex pheromone of the yellow mealworm bettleTenebrio molitor L. A scheme for synthesizing the racemic analogue of the pheromone from 4-methyltetrahydropyran has been developed. Institute of Organic Chemistry, Urals Branch, Russian Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 711–714, November–December, 1992.     

Synthesis ofS-(+)-hydroprene

A novel path toS-(+)-hydroprene (1) starting from the technical gradeS-(+)-dihydromyrcene (2, e.e. 50%) is proposed. The latter was selectively transformed intoS-3,7-dimethyloctanal (5) in three steps including hydroalumination. The reactions of5 with allyl- or methallylmagnesium chloride followed, respectively, either by oxygenation in the presence of PdCl₂/CuCl or by ozonolysis, affordS,E-6,10-dimethyl-3-undecen-2-one (7) which was treated with ethoxyethynylmagnesium bromide to give the title juvenile hormone analogue in 23% overall yield.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No 1, pp. 110–112, January, 1993.     

Pheromones of insects and their analogs. XXVII. Synthesis of 10-hydroxy-4,8-dimethyldeca-4E,8E-dienoic acid and of racemic 4,8-dimethyldecanal from geranyl acetate

10-Hvdroxy-4,8-dimethyldeca-4E,8E-dienoic acid and racemic 4,8-dimethyldecanal (components of beetle pheromones) have been synthesized from geranyl acetate.Institute of Chemistry, Bashkir Scientific Center, Urals Branch, Academy of Sciences of the USSR, Ufa. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 272–276, March–April, 1991.     

A convergent synthesis of octadeca-2E, 13Z-dienyl acetate, a pheromone component ofSynanthedon tipuliformis C.

A convergent synthesis of octadeca-2E, 13Z-dienyl acetate, a pheromone component ofSynanthedon tipuliformis C., has been developed. The synthesis is based on cross-coupling of 8-iodooct-2E-en-I-ol THP ether with dec-5Z-enyl bromide catalyzed by CuBr. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1529–1531, August, 1997.     

Use of enyne compounds in the synthesis of insect pheromones

A new approach has been developed to the synthesis of monogenic insect pheromones with acetogenin and macrolide structures, using the low reactivity of ozone and of 9-borabicyclo[3.3.1]nonane towards an acetylenic function as compared with a vinyl function.Institute of Organic Chemistry, Ufa Scientific Center of the Russian Academy of Sciences. Translated from Khimiya Prirodnykh Soedinenii, Vol. 33, No. 1, pp. 34–41, January–February, 1997.     

L-(-)-Menthol in the Synthesis of Key Synthons for Optically Active Methyl-Branched Insect Pheromones

A synthesis of optically active 4S-methylhexanal, 1-bromo-3S-methylheptane, and 1-bromo-3S-methylundecane, which are key synthons for several methyl-branched insect pheromones, that is based on chemically selective transformations of 6-tosyloxy- and 6-iodoisopropyl-4R-methylhexanoates that are available from L-(-)-menthol was proposed. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 592–593, November–December, 2005.