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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Sociedade Brasileira de Química
2004-01-01
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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 |
work_keys_str_mv |
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