Synthesis of (S)-(+)-2-methyl-4-octanol: male-specific compound released by sugarcane weevil Sphenophorus levis (coleoptera: curculionidae)

Journal of the Brazilian Chemical Society

Paulo H. G. Zarbin¹  Jefferson L. Princival¹  Alcindo A. Dos Santos¹  Alfredo R. M. De Oliveira¹ 

[1] ,Universidade Federal do Paraná Departamento de Química Curitiba PR ,Brazil

关键词: Sphenophorus levis;    aggregation pheromone;    2-methyl-4-octanol;    synthesis;    sugarcane weevil;    curculionidae;   

DOI  :  10.1590/S0103-50532004000200028

来源: SciELO

【 摘 要 】

(S)-2-Methyl-4-octanol (1) is a male-specific compound released by the sugarcane weevil Sphenophorus levis, being its biological activity associated with the aggregation behaviour of the species. Continuing our studies on the chemical ecology of this species, this work describes an expeditious synthesis of alcohol (1), starting from the easily available D-mannitol (2), in a route that employ the known (R)-glyceraldehyde acetonide (4) as key intermediate. GC analysis of an acetyl derivative of the final product, using a chiral stationary phase column, revealed an enantiomeric excess of 99.5%. Compound (1) has been identified as component of the male-produced aggregation pheromone in several curculionid species.

【 授权许可】

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