Straightforward Preparation of (2E,4Z)-2,4-Heptadien-1-ol and (2E,4Z)-2,4-Heptadienal

Autor:	Richard J. Petroski
Rok vydání:	2003
Předmět:	biology Organic Chemistry Biological pest control Alcohol biology.organism_classification Catalysis chemistry.chemical_compound Diorhabda elongata Tamarix spp chemistry Organic chemistry Weed Benzoic acid Leaf beetle
Zdroj:	Synthetic Communications. 33:3233-3241
ISSN:	1532-2432 0039-7911
Popis:	A concise synthesis of (2E,4Z)-2,4-heptadien-1-ol and (2E,4Z)-2,4-heptadienal is presented. Commercially available (Z)-2-penten-1-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-1-ol with LiAlH4. 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).
Databáze:	OpenAIRE
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