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

(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 synth...

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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:
Online Access:http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532004000200028
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spelling doaj-dddddb5363314cbd8e47d53445e90c762020-11-25T01:59:43ZengSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society0103-50532004-01-01152331334Synthesis of (S)-(+)-2-methyl-4-octanol: male-specific compound released by sugarcane weevil Sphenophorus levis (coleoptera: curculionidae)Zarbin Paulo H. G.Princival Jefferson L.Santos Alcindo A. dosOliveira Alfredo R. M. de(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.http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532004000200028Sphenophorus levisaggregation pheromone2-methyl-4-octanolsynthesissugarcane weevilcurculionidae
collection DOAJ
language English
format Article
sources DOAJ
author Zarbin Paulo H. G.
Princival Jefferson L.
Santos Alcindo A. dos
Oliveira Alfredo R. M. de
spellingShingle Zarbin Paulo H. G.
Princival Jefferson L.
Santos Alcindo A. dos
Oliveira Alfredo R. M. de
Synthesis of (S)-(+)-2-methyl-4-octanol: male-specific compound released by sugarcane weevil Sphenophorus levis (coleoptera: curculionidae)
Journal of the Brazilian Chemical Society
Sphenophorus levis
aggregation pheromone
2-methyl-4-octanol
synthesis
sugarcane weevil
curculionidae
author_facet Zarbin Paulo H. G.
Princival Jefferson L.
Santos Alcindo A. dos
Oliveira Alfredo R. M. de
author_sort Zarbin Paulo H. G.
title Synthesis of (S)-(+)-2-methyl-4-octanol: male-specific compound released by sugarcane weevil Sphenophorus levis (coleoptera: curculionidae)
title_short Synthesis of (S)-(+)-2-methyl-4-octanol: male-specific compound released by sugarcane weevil Sphenophorus levis (coleoptera: curculionidae)
title_full Synthesis of (S)-(+)-2-methyl-4-octanol: male-specific compound released by sugarcane weevil Sphenophorus levis (coleoptera: curculionidae)
title_fullStr Synthesis of (S)-(+)-2-methyl-4-octanol: male-specific compound released by sugarcane weevil Sphenophorus levis (coleoptera: curculionidae)
title_full_unstemmed Synthesis of (S)-(+)-2-methyl-4-octanol: male-specific compound released by sugarcane weevil Sphenophorus levis (coleoptera: curculionidae)
title_sort synthesis of (s)-(+)-2-methyl-4-octanol: male-specific compound released by sugarcane weevil sphenophorus levis (coleoptera: curculionidae)
publisher Sociedade Brasileira de Química
series Journal of the Brazilian Chemical Society
issn 0103-5053
publishDate 2004-01-01
description (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.
topic Sphenophorus levis
aggregation pheromone
2-methyl-4-octanol
synthesis
sugarcane weevil
curculionidae
url http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532004000200028
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