Scolytus 4-Methyl-3-heptanol

However, no cells in the males were keyed to the third compound (- )-cubebene which is produced by the host tree. Both sexes of 5. scolytus possess a majority of receptor cells keyed to either of the two male-produced compounds, (-)-threo-4-methyl-3-heptanol and the (-)-erythro-stereo-isomer, and in this species some cells were keyed also to (- )- -multistriatin (Wadhams et al., 1982). The relative sensitivities and specificities of these cells were determined in the same way as described for Ips species. Each cell was minimally activated by pheromone components other than its own key substance. The functional types of olfactory receptor cells discussed here for Scolytus, as with the cells of Ips, apparently are all keyed to the specific isomer of the pheromone compounds. The cells specialized to (- )-a-multistriatin are 1000 times less sensitive to the geometrical isomer d-multistriatin. However, the discrimination of the optical form of multistriatin seemed to be less pronounced. The substantially lower effect of the (-l-)-stereo-isomer (optical purity 99.5%), cannot be solely ascribed to contamination with the (- )-enantiomer. It implies that these cells in fact may also respond to (-l- )-multistriatin, although to a lesser extent. The cells keyed to methyl-heptanol are, however, highly optically specific in both species. 

Sn2 Reactions with epoxides and aziridines are also synthetically useful. An example of epoxide cleavage with an organocopper reagent with sp carbon moieties is the enantioselective synthesis of (3S, 4S)-4-methyl-3-heptanol (53), an elm bark beetle (Scolytus multistriatus) pheromone [42]. The chiral epoxy oxazolidine 51 [43], prepared from (R)-phenylglycinol, reacted with a propylmagnesium bromide-derived cuprate at —70 °C to afford the oxazolidine 52 in 74% yield (Scheme 9.12). Compound 52 was converted into the target molecular 53 by conventional procedures. 

Blight M. M., Wadhams L. J. and Wenham M. J. (1978) Volatiles associated with unmated Scolytus scolytus beetles on English elm differential production of a-multistriatin and 4-methyl-3-heptanol, and their activities in a laboratory bioassay. Insect Biochem. 8, 135-142. 

The terpenoid-exocrine theme emphasized by scolytid beetles was again evident when the chemical constitution of the secondary attractant for the smaller European elm bark beetle, Scolytus multistriatus, was elucidated. The aggregation pheromone was identified as a mixture of (-)-4-methyl-3-heptanol, 2,4-dimethyl-5-ethyl-6,8-dioxabicyclo [3.2.1]octane (multistriatin) (XXII), and (-)-a-cubebene (XXIII), a host-derived synergist (70). All three compounds are required for the maximum attraction of beetles. The inactive diastereomers of 4-methyl-3-heptanol and multistriatin did not inhibit the responses of airborne beetles. 

Such a sequence has been successfully used115 for the synthesis of 4-methyl-3-heptanol, the major constituent of the aggregation pheromone of the elm bark beetle (Scolytus multistriatus Marsham)117 and zir-butyM-methyltetrahydro-2-furanone118 known as quercus lactone or oak lactone. ... 

Recordings of olfactory receptor cells in Scolytus multistriatus and S. scolytus revealed the same degree of specialization as that found for Ips species. In males of S. multistriatus (attracted to the three-component mixture, multilure) the majority of receptor cells were keyed to either of the two compounds produced by females, (- )-a-multistriatin and (- )-threo-4-methyl-3-heptanol (Angst, 1981). 

Blight, M. M., Wadhams, L. J., Wenham, M. J. and King, C. J. (1979a) Field attraction of Scolytus scolytus (F.) to the enantiomers of 4-methyl-3-heptanol, the major component of the aggregation pheromone. Forestry, 52, 83-90. 

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