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

• Main Authors: Zarbin Paulo H. G., Princival Jefferson L., Santos Alcindo A. dos, Oliveira Alfredo R. M. de
• Format: Article
• Language: English
• Published: Sociedade Brasileira de Química 2004-01-01
• Series: Journal of the Brazilian Chemical Society
• Subjects: Sphenophorus levis; aggregation pheromone; 2-methyl-4-octanol; synthesis; sugarcane weevil; curculionidae
• Online Access: http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532004000200028

(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.