Enantioselective synthesis of (2R,3R,7S)-3,7 -dimethylpentadecan-2-ol, sex pheromone component of pine sawflies



Document title: Enantioselective synthesis of (2R,3R,7S)-3,7 -dimethylpentadecan-2-ol, sex pheromone component of pine sawflies
Journal: Journal of the Brazilian Chemical Society
Database: PERIÓDICA
System number: 000310924
ISSN: 0103-5053
Authors: 1
Institutions: 1Universidade Federal de Sao Carlos, Departamento de Quimica, Sao Carlos, Sao Paulo. Brasil
Year:
Season: Dic
Volumen: 11
Number: 6
Pages: 614-620
Country: Brasil
Language: Inglés
Document type: Artículo
Approach: Experimental, aplicado
English abstract The pine sawfly, Neodiprion sertifer (Geoffrey) (Hymenoptera: Diprionidae), is a widespread and economically important forest insect in North America, Japan and Europe. It has been demonstrated that the main sex pheromone components of this species are acetate or propionate of 3,7-dimethyl-2-pentadecanol (diprionol). We describe herein an enantioselective synthesis of (2R,3R,7S)-diprionol in 12 steps (7.5% overall yield), starting from commercial (-)-isopulegol
Portuguese abstract A mosca Neodiprion sertifer (Geoffrey) (Hymenoptera: Diprionidae) é uma importante praga em florestas de pinheiro no norte da Europa, Ásia e América do Norte. Os componentes majoritários do feromônio sexual desta espécie são acetatos ou propionatos do 3,7-dimetilpentadecan-2-ol (diprionol). Neste trabalho relatamos a síntese enantiosseletiva do (2R,3R,7S)-diprionol em 12 etapas (7.5% de rendimento total), partindo-se do (-)-isopulegol comercial
Disciplines: Química,
Biología
Keyword: Química orgánica,
Insectos,
Feromonas sexuales,
Síntesis enantioselectiva,
3,7-dimetilpentadecan-2-ol,
Diprionol,
Neodiprion sertifer,
Hymenoptera
Keyword: Chemistry,
Biology,
Organic chemistry,
Insects,
Sex pheromones,
Enantioselective synthesis,
3,7-dimethylpentadecan-2-ol,
Diprionol,
Neodiprion sertifer,
Hymenoptera
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