Rove beetle pheromone

In order to prepare the ( + )-Rove beetle pheromone. Node and colleagues reported a novel tandem Michael/Meerwein-Ponndorf-Werley reduction... 

Peschke, K. and Metzger, M. (1987). Cuticular hydrocarbons and female sex pheromones of the rove beetle, Aleochara curtula (Goeze) (Coleoptera Staphylinidae). Insect Biochem., 17,167-178. 

Stoeffler, M Maier, T.S., Tolasch, T. and Steidle, J.L.M. (2007). Foreign-language skills in rove-beetles Evidence for chemical mimicry of ant alarm pheromones in myrmecophilous Pella beetles (Coleoptera Staphylinidae)../. Chem. Ecol., 33, 1382-1392. 

Photolysis of the hypoiodite of hemiacetal 139 results in carbon-carbon bond cleavage to produce an iodolactone 140, Eq. 96 [83], The iodoalkyl side chain was subsequently homologated to afford the sex pheromone of the rove beetle. 

Intrasexual competition is also a very important factor influencing mating behavior insects have developed a series of strategies in competing for a potential mate and the necessary food resources. Young rove beetle males, Aleochara curtula, which are not sexually active yet, but need access to food sources avoid aggressive encounters and expulsion by mimicking the female sex pheromone 438). 

Enantiomerically pure lactonic pheromones 607-611, of the carpenter bee, blacktailed deer, Japanese beetle, rove beetle, and Oriental hornet, respectively, have been synthesized from racemic cyano alcohols of type 612. The key to the success of the overall approach is the facile separation of diastereomeric carbamates derived from cyano alcohols of type 612 by automated multigram LC. The chosen approach also facilitates the assignment of absolute configurations to the lactone enantiomers and their precursors. In the case of 607, direct determination of enantiomeric purity and absolute configuration is also possible using the chiral solvating agent 2,2,2-trifluoro-l-(9-anthryl)ethanol [439]. 

In 1949 Pavan isolated the substance he called iridomyrmecin from the Argentine ant Iridomyrmex humilis (now Linepithema humile). Iridomyrmecin, dolichodial and other monoterpenes with a methylcyclopen-tanoid structure are called iridoids (Figure 6.12). They act as defensive compounds in ants, stick insects, rove beetles and leaf beetle larvae. Some of the group (e.g. the isomer of nepetalactone shown in Figure 6.12) are also sex pheromones in aphids. Reaction of iridomyrmecin with... 

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