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Sociedade Brasileira de Química, SBQ, Journal of the Brazilian Chemical Society, 2(15), p. 331-334, 2004

DOI: 10.1590/s0103-50532004000200028

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Synthesis of (S)-(+)-2-Methyl-4-octanol: Male-specific compound released by sugarcane weevil Sphenophorus levis (Coleoptera: Curculionidae)

This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

(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.