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Syntheses of female sex pheromone precursors of pine sawflies species and of some structurally related methyl-branched long-chain 2-alkanols
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.ORCID iD: 0000-0002-5543-2041
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
Responsible organisation
2002 (English)In: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 28, no 6, 1237-1254 p.Article in journal (Refereed) Published
Abstract [en]

3,7-Dimethyl-2-undecanol, 3,7,9-trimethyl-2-tridecanol, and 3,7, 11-trimethyl-2-tridecanol were synthesized as racemic mixtures in moderate yields. The alcohols are known precursors of the female sex pheromones of the pine sawfly species Diprion nipponica, Macrodiprion nemoralis, and Microdiprion pallipes, respectively. Stereoisomeric mixtures of 3,8,12-trimethyl-2-tridecanol, erythro-(2R,3R,11R/S)-3,11-dimethyl-2-tetradecanol, 3,5-dimethyl-2-tetradecanol, and 5,7-dimethyl-2-tetradecanol, structurally related to sex pheromone alcohol precursors of pine sawfly species, were also synthesized in moderate yields. The key reaction in the syntheses was the ring opening of γ-butyrolactones by using different alkyl lithiums as nucleophiles.

Place, publisher, year, edition, pages
2002. Vol. 28, no 6, 1237-1254 p.
Keyword [en]
Synthses sex pheromone pine sawflies
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:miun:diva-2285DOI: 10.1023/A:1016289902732ISI: 000176803200011PubMedID: 12184400Scopus ID: 2-s2.0-0035990757Local ID: 1863OAI: oai:DiVA.org:miun-2285DiVA: diva2:27317
Available from: 2008-09-30 Created: 2008-09-30 Last updated: 2016-10-17Bibliographically approved

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Hedenström, ErikAndersson, Fredrik
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CiteExportLink to record
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Citation style
  • apa
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