Nom du corpus

Corpus Systématique Animale

Titre du document

Preparation of 8-methyl-2-decanol: General synthesis of diastereomeric mixtures of alkyl branched insect pheromones

Lien vers le document
Éditeur
Springer (journals)
Langue(s) du document
Anglais
Type de document
Research-article
Mots-clés d'auteur
  • Alkyl branched
  • pheromone
  • triple bond
  • alkyne
  • allene
  • isomerization
  • 8-methyl-2-decanol
  • 8-methyl-1-decyne
Nom du fichier dans la ressource
Insectes_v2b_00457
Auteur(s)
  • S. R. Abrams 1
  • A. C. Shaw 1
Affiliation(s)
  • 1) Plant Biotechnology Institute National Research Council of Canada, 110 Gymnasium Road, S7N OW9, Saskatoon, Saskatchewan, Canada
Résumé

A general method for synthesis of insect pheromones having alkyl branched carbon skeletons is demonstrated with the preparation of a diastereomeric mixture of 8-methyl-2-decanol, whose propionate is an attractant of someDiabrotica species. The procedure involves reaction of a ketone with lithium acetylide ethylenediamine complex to afford a propargylic alcohol containing the branch of the target molecule. Copper (1) mediated alkylation of the derived propargylic acetate with a primary alkyl halide yields a trisubstituted allene having the desired chain length, and isomerization with an alkali metal amide of either ethylenediamine or 1,3-diaminopropane, affords the alkyl branched terminal acetylene. The triple bond is converted to the methyl ketone and reduced to the methyl carbinol. The reactions proceed in good yield, and can be conveniently carried out on large scale. The method should prove useful for production of pheromone components in cases where diastereomeric mixtures can be employed.

Catégories Science-Metrix
  • 1 - natural sciences
  • 2 - biology
  • 3 - entomology
Catégories INIST
  • 1 - sciences appliquees, technologies et medecines
  • 2 - sciences biologiques et medicales
  • 3 - sciences biologiques fondamentales et appliquees. psychologie
  • 4 - industries agroalimentaires
Catégories Scopus
  • 1 - Life Sciences ; 2 - Biochemistry, Genetics and Molecular Biology ; 3 - Biochemistry
  • 1 - Life Sciences ; 2 - Agricultural and Biological Sciences ; 3 - Ecology, Evolution, Behavior and Systematics
  • 1 - Health Sciences ; 2 - Medicine ; 3 - General Medicine
Catégories WoS
  • 1 - science ; 2 - ecology
  • 1 - science ; 2 - biochemistry & molecular biology
Identifiant ISTEX
B97546A081060FBA9C86CD792240F45F32185D18
Revue

Journal of Chemical Ecology

Année de publication
1987
Présence de XML structuré
Non
Version PDF
1.3
Score qualité du texte
6.334
Sous-corpus
  • Insectes
Type de publication
Journal
ark:/67375/1BB-48MD8DTK-6
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