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Syntheses of the Sixteen Stereoisomers of 3,7,11-Trimethyl-2-tridecanol, Including the (2S,3S,7S,11R) and (2S,3S,7S,11S) Stereoisomers Identified as Pheromone Precursors in Females of the Pine Sawfly Microdiprion pallipes (Hymenoptera: Diprionidae)
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.ORCID iD: 0000-0002-5543-2041
2001 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 2001, no 2, 353-363 p.Article in journal (Refereed) Published
Abstract [en]

All sixteen stereoisomers of 3,7,11-trimethyl-2-tridecanol were synthesised in high stereoisomerical purities (> 95%), for use in the identification of the stereoisomers present in females of the pine sawfly Microdiprion pallipes (Fallen) (Hymenoptera: Diprionidae) as the precursor of the actual sex pheromone (which is the propionate), and also for investigation of the biological activities of the esters. The key step in the syntheses was the coupling of each of the enantiomers of cis-3,4-dimethyl-gamma -butyrolactone with each of the four pure stereoisomers of 1-lithio-2,6-dimethyloctanes. The four corresponding alcohols were obtained by lipase-catalysed (Amano PS) kinetic separation, based on selective acylation of either (2R/S,6S)- or (2R/S,GR)-2,6-dimethyl-1-octanol (obtained from the optically pure enantiomers of citronellal). Additionally, a mixture of the 16 possible stereoisomers of 3,7,11-trimethyl-2-tridecanol was also prepared.

Place, publisher, year, edition, pages
2001. Vol. 2001, no 2, 353-363 p.
Keyword [sv]
Feromoner, syntes
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:miun:diva-2279DOI: 10.1002/1099-0690(200101)2001:2<353::AID-EJOC353>3.0.CO;2-ZISI: 000166621900015Scopus ID: 2-s2.0-0035139029Local ID: 1859OAI: oai:DiVA.org:miun-2279DiVA: diva2:27311
Note

EUCHEM Conference on Ecological Chemistry: Chemical Communications, Aug 12-15, 1998, Sundsvall, Sweden

Available from: 2008-09-30 Created: 2008-09-30 Last updated: 2016-10-11Bibliographically approved

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Larsson, MichaelNguyen, Ba-VuHögberg, Hans-ErikHedenström, Erik
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