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Synthesis and lipase catalysed stereoselective acylation of some 3-methyl-2-alkanols, identified as sex pheromone precursors in females of pine sawfly species
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.
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
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2002 (English)In: Journal of The Chemical Society, Perkin Transactions 1, ISSN 1472-7781, Vol. 2002, no 15, 1810-1817 p.Article in journal (Refereed) Published
Abstract [en]

Several 3-methylalkan-2-ols precursors to sex pheromones of Diprion pini, Gilpinia pallida, Gilpinia frutetorum, Diprion nipponica, Macrodiprion nemoralis and Microdiprion pallipes were synthesised as stereoisomeric mixtures in moderate to good yields. The key reaction sequence in the syntheses was the ring opening of either cis- or racemic trans-epoxybutane using a higher order cyanocuprate as nucleophile followed by a highly efficient lipase catalysed stereoselective acylation of the obtained 3-methylalkan-2-ol. The biologically active species specific stereoisomer was synthesised as a single stereoisomer in high stereoisomeric purity, as one in a mixture of two or as one of four stereoisomers when the appropriate 3-methylalkan-2-ol was stereoselectively acylated using a Pseudomonas sp. lipase as catalyst.

Place, publisher, year, edition, pages
2002. Vol. 2002, no 15, 1810-1817 p.
Keyword [en]
Synthesis lipase catalysed sex pheromone pine sawfly
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:miun:diva-2284DOI: 10.1039/b201395aISI: 000177073300014Scopus ID: 2-s2.0-0035995717Local ID: 1862OAI: oai:DiVA.org:miun-2284DiVA: diva2:27316
Available from: 2008-09-30 Created: 2008-09-30 Last updated: 2016-10-17Bibliographically approved

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Hedenström, ErikEdlund, HelenLund, Susan
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CiteExportLink to record
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Citation style
  • apa
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