Blacktail deer

Humans and insects can discriminate enantiomers of the same compound (Friedman and Miller, 1971 Russell and Hills, 1971) (Table 2.1). Blacktailed deer Odocoileus hemionus columhianus) discriminate between the two geometric isomers and somewhat between the enantiomers of the deer lactone (Fig. 2.2) (Brownlee eta/., 1969 Muller-Schwarzeeta/., 1976,1978a). Young male Asian elephants have more (+) than (-) enantiomer of frontalin in their temporal secretion. Their secretion and(+)-frontalin affect conspecifics little. However, the nearly recemic enantiomer mix from mature bulls attracts ovulating females and repels males (Greenwood etal., 2005)... 

Melchiors, M. A. and Leslie, C. A. (1985). Effectiveness of predator fecal odors as blacktailed deer repellents. JournalofWildlifeManagement 49,358-362. 

The response to metatarsal odor consists of increased alertness. Only females show a response and they do so to both male and female metatarsal scent (254), but Odocoileus virginicus, the white tailed deer, does not exhibit this alarm behavior system to the same degree (299). It has also been observed that two subspecies of blacktailed deer, O. he-mionus columbianus and O.h. hemionus, can distinguish each other in this manner. Such discrimination may be important in sexual isolation of the species (254). 

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]. 

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