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ARS Home » Midwest Area » Peoria, Illinois » National Center for Agricultural Utilization Research » Crop Bioprotection Research » Research » Publications at this Location » Publication #135984
Title: STRAIGHTFORWARD PREPARATION OF (2E,4Z)-2,4-HEPTADIEN-1-OL AND (2E,4Z)-2,4-HEPTADIENAL

Author
item Petroski, Richard

Submitted to: Synthetic Communications
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 6/11/2003
Publication Date: 6/17/2003
Citation: PETROSKI, R.J. STRAIGHTFORWARD PREPARATION OF (2E,4Z)-2,4-HEPTADIEN-1-OL AND (2E,4Z)-2,4-HEPTADIENAL. SYNTHETIC COMMUNICATIONS. 2003. v. 13(18). p. 3233-3241.

Interpretive Summary: Saltcedar (Tamarix spp) is an invasive bushy tree found along rivers in the Western United States. Because of ecological concerns about the use of herbicides, the Saltcedar leaf beetle has been approved as a biological control agent. There is a need to monitor dispersal of the beetle from sites of release. Recently, male-specific volatile compounds from the Saltcedar leaf beetle have been identified. These compounds are likely to be part of the pheromone of the Saltcedar leaf beetle. A straightforward synthetic route was developed to prepare sufficient quantities of the compounds for further evaluation by scientists. These compounds might be used as attractants in baited traps to monitor areas of saltcedar for the presence and numbers of the beetle. This research benefits pheromone scientists and other entomologists by providing access to chemicals that will be used along with a beneficial insect, to control a significant invasive weed.

Technical Abstract: A concise synthesis of (2E,4Z)-2,4-heptadien-l-ol and (2E,4Z)-2,4-heptadienal is presented. Commercially available (Z)-2-penten-l-ol was converted to ethyl-(2E,4Z)-2,4-heptadienoate by reaction with activated MnO2 and (carboethoxymethylene)triphenylphosphorane in the presence of benzoic acid as a catalyst. Ethyl-(2E,4Z)-2,4-heptadienoate was converted to (2E,4Z)-2,4-heptadien-l-ol with LiA1H4. The alcohol was partially oxidized to (2E,4Z)-2,4-heptadienal with MnO2. The title compounds are male-specific, antennally active volatile compounds from the Saltcedar leaf beetle, Diorhabda elongata Brulle (Coleoptera: Chrysomelidae) and have potential use in the biological control of the invasive weed saltcedar (Tamarix spp).