Journal of the Brazilian Chemical Society
On-line version ISSN 1678-4790
ZARBIN, Paulo H. G.; PRINCIVAL, Jefferson L.; SANTOS, Alcindo A. dos and OLIVEIRA, Alfredo R. M. de. Synthesis of (S)-(+)-2-methyl-4-octanol: male-specific compound released by sugarcane weevil Sphenophorus levis (coleoptera: curculionidae). J. Braz. Chem. Soc. [online]. 2004, vol.15, n.2, pp.331-334. ISSN 1678-4790. http://dx.doi.org/10.1590/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.
Keywords : Sphenophorus levis; aggregation pheromone; 2-methyl-4-octanol; synthesis; sugarcane weevil; curculionidae.