European bark beetle

The fungus responsible for Dutch elm disease is spread by European bark beetles when they burrow into the tree Other beetles congregate at the site attracted by the scent of a mixture of chemicals some emitted by other beetles and some coming from the tree One of the compounds given off by female bark beetles is 4 methyl 3 heptanol Suggest an efficient synthesis of this pheromone from alcohols of five carbon atoms or fewer... 

CgH.gO, Mr 130.23, bp. 160-161 °C. The (3S,45)-iso-mer, [a]n -23.3° (hexane), an important component of the aggregation pheromone (see pheromones) of bark beetles of the genus Scolytus, e.g. the smaller European bark beetle. S. multistriatus is a carrier of the fungus Ceratocystis ulmi causing death of elm trees. It also occurs in ants. The (3/ ,45)-stereoisomer is a trail pheromone of the ant Leptogenys diminuta, see also multistriatin. 

The European bark beetle produces a pheromone that causes beetles to congregate. Describe two ways that the compound could be synthesized by a Grignard reagent. 

Claisen rearrangement of glycolates. Two laboratories 2 have reported that allylic glycolate esters undergo Claisen-Ireland rearrangement (6, 276-277) with useful diastereoselectivity. This rearrangement was used in a synthesis of 1, the aggregation pheromone of the European elm bark beetle.1... 

Often related insect species are not all sensitive to a particular allomone. For example, juglone is a feeding deterrent to the smaller European elm bark beetle (Scolytus multistriatus) but not to the closely related hickory bark beetle (Scolytus quadrispinosus) (106,107). 

Stereoselective reactions with aldehydes. The related (E)-2-pentenyltin reagent 2 also reacts with aldehydes to form predominantly erythro adducts such as 3. This reaction was used for a stereoselective synthesis of an aggregation pheromone (4) of the European elm bark beetle.1... 

B) Western balsam bark beetle, Dryocoetes confusus formation of endo-brevicomin [(1 F ,5S,7S)-7-ethyl-5-methyl-6,8-dioxabicyclo[3.2.1 ]octane] from ( )-6-nonen-2-one (Vanderwel et a/., 1992a) (C) Spruce beetle, Dendroctonus rufipennis formation of frontalin [(1S, 5fl)-(-)-1,5-dimethyl-6,8-dioxabicyclo[3.2.1]octane] from 6-methyl-6-hepten-2-one (Perez ef a/., 1996 Francke etai, 1995 Francke and Schulz, 1999) (D) European elm bark beetle, Scolytus multistriatus hypothetical formation of oc-multistriatin [(1 S,2F ,4S,5F )-(-)-2,4-dimethyl-5-ethyl-6,8-dioxabicyclo[3.2.1]octane] from 4,6-dimethyl-7-octen-3-one (Francke and Schulz, 1999) and E The colored... 

Birch M. C., Paine T. D. and Miller J. C. (1981) Effectiveness of pheromone masstrapping of the smaller European elm bark beetle. California Agriculture 35, 6-7. 

Gore W. E., Pearce G. T., Lanier G. N., Simeone J. B., Silverstein R. M., Peacock J. W. and Cuthbert R.A. (1977) Aggregation attractant of the European elm bark beetle, Scolytus multistriatus, production of individual components and related aggregation behavior. J. Chem. Ecol. 3, 429 446. 

Mori K. (1974) Synthesis of (15 2R 45 55)-(-)-a-multistnatin the pheromone in the smaller European elm bark beetle, Scolytus multistriatus. Tetrahedron 32, 1979-1981. 

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. 

T1 bark beetles,489 Vespa crabro, European hornet 490... 

Pougny, J R, Sinay, P, (35,45) -methylheptan-3-ol, a pheromone component of the smaller european aim bark beetle synthesis from D-glucose, J. Chem. Res., 1, 1982. 

Eggplant, 93-94 European elm bark beetles, 288 Flatheaded borers... 

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