Pheromones oxygen containing

The diols 4 and 6-10 are particularly suited for the preparation of small molecules, like insect pheromones, that contain relatively few chiral carbon atoms in their framework and whose chirality is due to oxygen substitution.From related isopropyli-dene structures it is possible to synthesize the chiral C, C and Cg carbonyl compounds (11)-(14) by ozonolysis, that are convertible into the a-epimers (15)-(18) by base treatment. Furthermore, the number of synthons that are potentially available is increased by the adducts accessible from (11)-(18) by reaction with suitable carbon nucleophiles under conditions allowing control of the stereochemistry by the two oxygen functions. 

Lepidopteran pheromones generally contain 10-20 carbon atoms with a single oxygenated functional group such as acetate, alcohol or aldehyde most have one or more sites of unsaturation. The compounds are quite volatile, and some, particularly the aldehydes, are unstable in air. All of these factors contribute to the need to formulate the pheromones in a... 

Eiceman, G.A. Tadjikov, B. Krylov, E. Nazarov, E.G. Miller, R.A. Westbrook, J. Funk, P., Miniature radio-frequency mobility analyzer as a gas chromatographic detector for oxygen-containing volatile organic compounds, pheromones and other insect attractants, J. Chromatogr. A 2001, 917, 205-217. 

Structurally, beetle pheromones are difficult to classify. They are often fatty acid or oxygen-containing terpene derivatives, occasionally with a complex polycyclic structure. 

The practice and theory of enantioselective CGC was comprehensively reviewed. Racemic oxygen-, nitrogen- and sulfur-containing selectands can be separated without prior derivatization into enantiomers by CGC on optically active metal(II) bis[3-(perfluoro-acyl)-(lR)-camphorate] (61) selectors. Peak inversion is obtained when the selectors with opposite configuration are employed. Applications pertain to chiral analysis in asymmetric synthesis, enzymatic reactions, pheromone and flavor chemistry. ... 

Twenty-two pheromones and kairomones and two synthetic analogues are now listed in The Pesticide Manual (Tomlin, 2000). Most of them are long aliphatic unsaturated compounds, with substituents containing oxygen, e.g., esters, alcohols, ketones, and aldehydes. 

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